These days George Burley can walk to Portman Road from his front doorstep in 20 minutes, or perhaps drive it in five. He can watch every home game virtually unremarked upon, not that friendly faces are scarce. His old chairman David Sheepshanks might sit next to him in the Britannia Stand, just yards from the dugouts, and there are always other old faces passing through. Occasionally a supporter might stop him: they would give anything to have him back, they say, anything for nights like that one, anything for relief from the sighs, silences and empty blue seats that make those occasions harder to grasp for by the day. It is just talk, everyone knows that: Burley is over 60 now and family is more important; it is only a harmless way of preserving the memory and the meaning. Time has moved on, and pining for what used to be is a very different thing to recreating it.

At the turn of the millennium a walk along a similar route, through an unremarkable estate and then on into town, was more about the building of memories. Around every corner, something new. The experience of supporting a football club in your mid-to-late teens, every minor victory magnified and every small defeat cause for despair, mirrors the coming-of-age process uncannily. When the ups and downs occur all at once they become inextricably bound and that was life in Ipswich at the age of 17: underage pubs, mock A-Levels, football in the park, fake IDs, petty squabbles, shifts at Woolworths, tentative approaches to girls. And Ipswich in the play-offs.

Back then, the sense of adventure felt like a right. Since the Bobby Robson era Ipswich had never quite fallen upon a fallow period long enough to suggest their star had been completely extinguished and most years involved a drama of some kind: a promotion to the Premier League in 1992, a final-day reprieve in 1994, ignominy in 1995, seventh place and seat-throwing Millwall fans on the final day in 1996. The three seasons that followed, which brought largely free-flowing football and top-six finishes in the second tier followed by disappointments of varying gravity, were felt all the more bitterly when you were a jumbled mixture of hormones, hopes and expectations, but they served a perfect role. Ipswich were thrusting, relevant, proud, optimistic, deeply flawed; it all became hard to separate from the developing, overly-absorbed sense of self.

By the time 2000 came around, the credit boom was taking hold; the pubs were heaving on Friday nights, shots of garish colours went for £1 and beer for little more. On the evening of April 28, they queued out of the door at the Flour and Firkin to watch second-placed Manchester City, ahead of Ipswich by two points, play Birmingham in their penultimate match. Joe Royle’s team squeaked home. The thought, 17 years on, of the town’s hostelries bursting at the seams to watch two of Ipswich’s competitors feels like a trick of the memory; although it was partly born through a time of drinking out, spending money and damning the consequences, it also spoke of a lurking fear. Nobody wanted to go through the play-offs again.

Burley’s Ipswich, playing some marvellous football and clicking once more after a disjointed spring, matched City’s six points over those final two games but that was never going to be enough. It meant Bolton, who finished sixth again, would meet Ipswich, third again, for the second year in a row in the play-offs. The first had brought tears from a 16 year old who watched Kieron Dyer force extra-time with an improbable header from the edge of the box before a cute, canny Bolton broke and scored a decisive away goal through Bob Taylor.

Who could stomach more of that? It felt like failure although Ipswich, reinvesting wisely the £6m Newcastle subsequently paid them for Dyer, looked a more rounded team for most of 1999-2000. Their biggest difficulty came in accommodating Marcus Stewart, whose stunning arrival for £2.5m from fellow contenders Huddersfield had been intended to fire them over the line but instead, after a wonderful start in which he scored twice in as many games, resulted in the disruption of a sleekly-functioning attack in which David Johnson, James Scowcroft and Richard Naylor had been playing the best football of their relatively young careers.

There had been signs of improvement, though, in those final two games – a 3-1 win at already-promoted Charlton and a Johnson-inspired victory over Walsall that had, briefly, promised to be a rather greater occasion when Blackburn took the lead against City. For the 3,000 supporters who mustered themselves for a baking May lunchtime in Greater Manchester there was enough cause to believe that Bolton – now managed by Sam Allardyce, who had heaved them into the play-offs after inheriting a side struggling to recover from the previous campaign’s eventual Wembley defeat – would prove less of a tormenting obstacle this time as long as any mental hurdles were cleared.

The 2-2 draw that followed was not quite as good a result as it looked – the away goals rule that did for Ipswich the year before had, after a vote among Football League clubs led by an exasperated Sheepshanks, been shelved – but the momentum went only one way. Ipswich were battered for much of the first half at the Reebok Stadium, quickly going two soft goals down to Dean Holdsworth and Eiður Guðjohnsen. Johnson, who had scored 22 league goals that season, went off with a neck injury and the veteran defender Tony Mowbray, semi-retired until being parachuted back into the side with remarkable effect after a 4-1 home defeat to QPR in October, was also forced to withdraw after a blow to the head. The scene on the pitch was chaotic; the tears were, even if you were a year older, being choked back.

In the 36th minute a bolt from the blue arrived and nothing was ever quite the same. Stewart, who had not scored since February and was becoming the subject of discontented murmurs from fans due to occasional sightings in local nightspots, took a header from Matt Holland first-time with his left foot and swiped a vicious, dipping 30-yard volley past Jussi Jääskeläinen. It would have flown over the bar nine times out of ten; instead Ipswich were revitalised and, shooting towards the away support in their bright orange away shirts, dominated the rest of the game. When the equaliser came it was via a masterpiece from Stewart, who would soon enough make his name with a series of similar finishes in the tier above. When he checked after taking the ball around Jääskeläinen it seemed to expose his one-footedness; instead it turned out that, after transferring the ball onto his left, he had worked the perfect angle for himself and the finish, bent into the far corner a millisecond before the goalkeeper could recover, was the kind that you fear will go wrong upon every replay. 

It made the journey home a giddy one and the next three days were little different. Allardyce, relatively callow at 45 but never scared of a niggle, had been rattled sufficiently to crank up the mind games before the Portman Road fixture. “I hope that going into the play-off scenario for the fourth time on the trot will weigh down on the players mentally, so we can capitalise on that,” he said. “I’ve known George Burley a long time, but there is no sentiment in this game and if we can build upon their bitter disappointment, then so be it.”

Burley, rarely one for a media soundbite and better known for a narrow range of variations upon “all credit to the lads”, gave the impression Ipswich might fulfil Allardyce’s wish when suggesting his side “should have home advantage in a one-off match”, but switched to the positives and the suggestion they were “a stronger team going forward” was as close to a bout of chest-beating as he had ever come.

May 17 was one of those wriggly, fidgety days when nobody really achieves anything. It was, according to play-off type, warm and balmy; the walk to the stadium taut and tense, ready to wind up or all the way down. You expected the best but were deeply afraid of the route there; this was the period that defined the play-offs as wild, rollercoaster affairs with little regard for norms or decorum. It is a reputation that does not always hold true now, particularly in a Championship of far more tactical acumen and circumspection, but in 2000 you were heading straight for the eye of the storm. You knew it but, as with all of the turf wars and battling for pack supremacy that an active part in teenaged life entailed, you plunged straight into it anyway.

Match days tended to bear the hallmark of the clubbable Sheepshanks, an Old Etonian with a far greater common touch than he is generally given credit for. Sheepshanks had appointed Burley in 1995; the pair had slowly created something vibrant and compelling in a town that had enough memories of success to draw upon to make a reawakening more than possible. Portman Road, its capacity 8,000 smaller back then, could be a raucous place when close to full but it retained some eccentricities. “Hi Ho Silver Lining” would play shortly before the teams came out, which seemed far from sinful when the sun was shining and the football was likely to be good, while the final song before kick-off would be a remastered version of “Singing the Blues” that, although low on production value and high on the cringe scale, was still able to unite 20,000 people in its unique way. It all made for a bright, generally happy place, one that had known its share of knocks but that felt assured of its place in history, too.

Johnson was passed fit despite prior assumptions that he would miss out. Guðjohnsen did not make the journey due to a knock of his own and you wonder how that may have informed his team’s approach. Bolton, who had snarled their way to victory the year before with Colin Todd in charge and retained a similar sense of menace under Allardyce, were outmanoeuvred in the opening stages and Johnson, seizing onto a loose pass, worked Jääskeläinen within minutes. The noise was as shrill as it had ever – has ever – been. Nobody could live with a jinx like this for another year.

It said plenty for the maelstrom that had been expected that, certainly for a row of nervous but unspeakably excited observers in Block M, Bolton’s opening goal in the sixth minute seemed more like an inevitable complication than an important blow. Richard Wright, an outstanding goalkeeper whose career should never have descended into light mockery, was distracted by Robbie Elliott’s jump beneath a looping cross from Michael Johansen, and duly fumbled. Holdsworth reacted quickest and poked a shot that trickled, almost apologetically, into the far corner. Ipswich claimed a foul; the referee, Barry Knight, was correct not to give one.

Mark that sentence, because it was a decision by Knight that nobody could really argue with. The match, which had felt edgy from kick-off, descended into chaos within 12 minutes of Holdsworth’s opener and Knight, a well-regarded official who would be promoted to the Premier League’s Select Group the following year, had little or no hope of jamming the lid back on.

The first flashpoint came when Jim Magilton, playing a sharp one-two with Johnson, burst into the area from midfield and was checked by Holdsworth, who had offered no tackle but clearly left his body in the way. Knight pointed to the spot, and Bolton were incensed. They claimed Magilton had dived; in fairness the Northern Irishman was not always averse to a little gamesmanship but in this case the offence looked clear cut. Chief among the complainants was Mike Whitlow, a battle-worn 32-year-old defender with jagged teeth and a stare to raise the dead. Whitlow appeared to offer Magilton a fight in the privacy of the changing room; Magilton demurred, eventually sent the penalty to Jääskeläinen’s right, and exchanged more words with his opponent in the immediate aftermath. The tone had been set. The exchanges flowed from end to end, Bolton’s emphasis on physique quite evident against Ipswich’s smaller, more mobile players. The visitors were not short of technical quality; Claus Jensen, Allan Johnston, Johansen and even Holdsworth could deal with the ball but Allardyce’s plan was clear: stop Ipswich playing, via whatever means.

The most effective way would be to score again, and when Holdsworth did that six minutes before half-time you wondered how much longer Ipswich could roll with the punches. This time Knight was rather more generous to Bolton, awarding a soft free-kick to the left of centre for a foul by Gary Croft on Johnson. Wright seemed to have positioned himself well, to the exposed side of his wall, but at the last moment took two steps to his right and was punished when Holdsworth, whipping his foot around the ball beautifully, bent a low shot in off the post. The gap Wright had left was crucial; the error seemed to be too, because Ipswich had again showed that, for all their patience and control of possession, they had a mistake in them when it counted.

Bolton went in at the interval 2-1 up, and had they done so by seeing the first half out calmly they may well have won the game. Instead they conceded a second penalty as the clock ticked down when Magilton, behind all of Ipswich’s best work, wrong-footed the defence by leaving a Mark Venus pass. It freed Stewart, who was then clattered by a thudding challenge from Paul Ritchie. Again, Knight awarded the penalty; Ritchie had taken some of the ball, along with a sizeable chunk of the man. It sent Bolton over the edge as Knight, retreating to a slightly unwise position directly in front of the away fans, was surrounded by a pack of white shirts led by Whitlow, Warhurst and Guðni Bergsson. Johansen, attempting to drag the latter back by the shirt, could do nothing to stop his team-mate piling in. It was intimidation of the lowest order; Knight had presumably decided Ritchie’s challenge was too aggressive or, perhaps, that his foot was over the ball. Magilton prepared to step up again, Warhurst attempting to continue the debate with him. It had taken two minutes for a pretence at calm to be reached and this time Jääskeläinen made an excellent save, tipping the shot behind to his right. The whistle was blown almost instantly; Bolton were in front but it was clear that Allardyce had wound them up sufficiently to be a danger to themselves.

Magilton aside, Ipswich did not really possess a player who could wind opponents up. It was a failing of Burley’s sides and one others sought to exploit; it did, though, mean they tended to operate with clear heads and that paid dividends four minutes into the second half. Ipswich, as was their specialty, kept the ball assiduously before cranking through the gears quickly, Johnson again finding Magilton in the box with a sharp one-touch flick. Magilton never quite seemed to have control of the ball, but Warhurst and Whitlow both hesitated for a split second, appearing to believe each other in control of the situation. One of them should have been; instead, Magilton worked space on the angle and blasted into the net at the near post.

Within a minute Ipswich self-destructed again, although, as with so many moments from this game, there was an asterisk next to the goal. Bolton’s anger with Knight would dominate the narrative around what happened here for years; they benefited from a greater number of important calls than history tends to dredge up. Portman Road was throbbing now and when, almost straight after the restart, Johnson rolled Mark Fish and was pulled down, a free-kick on the right-hand corner of the area looked likely. Instead Knight ruled, very harshly, that Johnson had been backing in; Jääskeläinen promptly punted the ball long and Holdsworth, who was playing superbly, chested down for the onrushing Johnston. It bounced up perfectly and the finish, laced up and beyond Wright from 25 yards, was perfect. Bolton had done it again.

For the first time, Portman Road went flat. You can only gather yourself, both physically and mentally, to go again so many times. Johnson was denied by Jääskeläinen minutes later but there followed half an hour of frustration and atrophy. Ipswich looked spent, out of ideas; the influential Scowcroft went off with a hamstring injury and it was Jensen, put through by Elliott, who should have sealed matters for Bolton only to be denied by Wright’s left leg. Bolton blocked, niggled, fouled but – for now – showed little of their earlier combustibility. They were seeing this out expertly.

Yet there was never quite the sense that it was done. Ipswich had been here, almost exactly to the letter, a year before and at least managed to drag things out into extra-time. As the clock passed 90 minutes, and with Mowbray by now deployed up front, another group of Ipswich supporters, gathered behind the North Stand, were experiencing things their own way. One of them, drunk on desperation, screamed, “If we score now I’m getting the club badge tattooed on my arse.” Seconds later, and one more punt from Mark Venus. Mowbray, somehow finding the composure both to win his header and angle his body to direct it into Magilton’s path, met the delivery while falling. Magilton, controlling on the thigh 16 yards out, had a split-second of time but had to act instantly. Reports afterwards said he had shinned the ball; it looks more that Magilton, such an artful footballer, cut across it to find the only unattended space between him and Jääskeläinen. The Finn was rooted, unsighted. Magilton’s shot fizzed into the corner; the roof was raised; a tattoo parlour had a new customer, true to his word, the following morning.

Magilton had never before looked like scoring a hat-trick. He was not really that kind of midfielder, more given to continuity and construction than heroic dashes from deep. But he had been like a man possessed here; he later described the night as “one of the highlights of my career” but, for its sheer heroism, implausibility and timing, it seems impossible to outdo. The image of that third goal returns so readily; it is, from 27 years’ attendance, the one that crystallises everything; the frayed perfection Burley will never begin to try to emulate again, the pent-up frustration of adolescence and the realisation that everything might just turn out OK but, at the same time, can never be quite this good again.

“How much more can anybody take inside this ground at the moment?” asked the commentator on the local television highlights package. It was as draining, as exhausting and bewildering as football can get and there was still time for something more. Ipswich went in search of a winner and Stewart, taking the ball away from Whitlow and approaching the box, was bumped cynically from behind by the defender’s knee. It was not a goal-scoring opportunity – there were two more defenders between Stewart and the goal – but Whitlow, who had not appeared to be cautioned earlier despite his volley of invective at Knight, was shown a straight red card. He looked too bemused to repeat the salvo, shaking his head and walking away slowly; this was probably Knight’s most perplexing decision of the evening but, even then, it was hard to say Whitlow had not deserved two yellow cards.

It was now Ipswich’s to lose, not that they were incapable of another implosion. The air was pregnant with the knowledge that something seismic, whatever it was, would shortly pass. Extra-time was managed calmly and with a strange, displacing sense of inevitability, although that looked more the case when contrasted with Bolton’s next, more prolonged, implosion. When Venus pumped another direct ball forwards – a tactic Ipswich, despite their aesthetic gifts, were not afraid to employ when it suited them – Naylor, who had replaced Scowcroft, won the header and Johnson, jumping with Ritchie, came out on top in his challenge too. The ball seemed to have looped harmlessly towards Jääskeläinen but Ritchie, in a rush of blood that looks harder to explain with each replay, hauled Johnson down by the neck. It was such a bizarre, needless action; the play had been going nowhere and Knight, awarding the easiest of Ipswich’s three penalties, had little choice but to act again. Bolton’s complaints were again prolonged but, perhaps partly due to Whitlow’s absence, largely perfunctory. Magilton passed up on the chance for a fourth goal; surprisingly it was Jamie Clapham, a neat left wing-back who was sometimes seen as embodying Ipswich’s lack of nastiness and killer instinct, who stepped up. Clapham scored; Ipswich led at last, although the celebrations on the pitch were noticeably more cautious and restrained by those that had greeted any of Magilton’s equalisers.

In a footballing sense, Bolton had gone. But as Ipswich, now confident and cruising, played around them a sense of menace was detectable in their pressing of the ball. Feet were left in, rash challenge hurdled and then, as the substitute Martijn Reuser took the ball near the corner flag, Elliott felled him with a tackle born of frustration and sheer spite. He had been booked already; now he was off and Bolton were down to nine.

There remained the nagging feeling Ipswich could throw this away, even as they exploited the open spaces at will. That concern was allayed with a minute of the second period to go when the powerful Naylor, shrugging off Ritchie, squared to an unattended Reuser. The Dutchman brought the ball forward and made no mistake; there could be no more errors from Ipswich now, either. It was 5-3 and they would be going to Wembley.

Nobody has a very lucid account of what happened after full-time. There is the memory of being bear-hugged on the Portman Road pitch, quickly swamped from all side, by the maths teacher from school to a soundtrack of “Que sera sera”. This being Ipswich, acquaintances were visible at every glance; hugs followed, more tears, and then the momentary flatness of finding the bars in the town centre closed.

Allardyce, meanwhile, was laying into the television cameras and savaging Knight’s performance. He, Whitlow, Warhurst, Bergsson, Ritchie, Johansen and Jimmy Phillips would all be brought to book that summer by the FA, who deemed that Bolton had not controlled their players. The wound festered for years, perhaps still does; in an interview with FourFourTwo in 2005, long after he had brought Bolton up and established them as a respectable Premier League side, he admitted he held a “grudge” about what he termed “the worst refereeing performance in the history of football”.

He proceeded to excuse the reactions of his players, who had been shown 10 yellow cards to add to the punishments delivered to Whitlow and Elliott. “What they don’t understand is that if a player reacts badly it’s often down to the referee,” he said. “My players play under my rules and my discipline, but when they walk over the white line, the referee takes over. If he can’t referee correctly, if he constantly provokes players with wrong decisions, you’re going to get a reaction. Referees are sometimes more responsible for player reaction and crowd violence than players.”

It would have been more accurate to say that Allardyce’s rules and discipline had been wide of the mark; it was, however the rule change sought by Ipswich that had played as decisive a role as any. The previous year, Magilton’s moment of wonder would have been a mere consolation; without the away goals tie-breaker, it won its place in folklore.

The win cast a monkey off the back of Ipswich’s players and fans. They went on to beat Barnsley 4-2 at Wembley in another see-sawing, knockabout tie that added to the play-off legend, but in the intervening fortnight you were hard pressed to find anybody who thought they wouldn’t do it now. Reuser, a throwback of a player who had joined from Ajax that March and made up for a lack of fitness and aggression with moments of genius that earn him something near to deity status in Suffolk, scored the clinching goal and the following day Sheepshanks could be seen alongside Burley on the town hall balcony, screeching “We are Premier Leeeeaaague.” You did cringe then; now, you just wish the moment could have lasted forever.

Sheepshanks and Burley took Ipswich to fifth place in the Premier League before everything fell apart, precipitating a decline that has seen the club’s standing hit a 50-year low. Magilton, who ought to be looked upon with unreserved fondness, managed the team for three years until Roy Keane’s arrival in 2009, ushered aside by the owner Marcus Evans – assisted by the vitriol of supporters with short memories – in the days when £5m of wise transfer spending looked as if it should get you out of the Championship. 

Nobody who was there on May 17 has had a night like it since and if, almost two decades on, another comes around it has little chance of awakening the exhilarating, raw, exploratory feelings that ran alongside it. It doesn’t really matter. Few would begrudge a touch of mournfulness in Burley and Sheepshanks when they sit together now, in a half-full ground watching an under-resourced side; to a supporter midway through his 18th year in 2000, though, the magnitude of what they gave was far more significant than everything that was later taken away.