Today is the 20th anniversary of the Blues’ glorious 4-2 Wembley play-off final victory over Barnsley, so TWTD caught up with George Burley to see how he remembers the day and that period of his time as manager of the club.
Town finished 1999/00 in third in what was then known as the First Division having narrowly missed out on automatic promotion and were facing the play-offs for the fourth successive year.
Burley says there was pressure given that context but that there wasn’t any undue negativity as a result of the previous disappointments.
"I think there’s always pressure at a club like Ipswich with the history,” Burley said. "I enjoyed a lot of that as a player in probably the club’s best era under Sir Bobby Robson.
"You’re always as a club looking to get back into the Premier League, looking to get success and bringing players through and winning games and playing to your philosophy.
"As you say, three missed opportunities before where we were close, a number of times close to getting automatic promotion and then missing out and then missing out in the play-offs.
"It was a build-up, but I think we all grew together, the fans, the players, the young players coming through the academy into the team, players I’d brought in from other lower league clubs.
"I think we all grew together and we all handled the pressure and, of course, it eventually worked out.
"But it wasn’t a situation where we were so frustrated that we thought it would never happen because I kept saying it was great that the fans knew where we were coming from, we knew every season we had to sell a player or two to balance the books and we knew that we were going to concentrate on playing a certain way and bringing young players through.
"I think the fans and the players that came to the club, the youngsters coming through the academy all bought into it and we all worked hard together to achieve our ambition.”
That requirement to cash-in on players to make ends meet saw Kieron Dyer sold to Newcastle United in the summer of 1999 for an initial £6 million with the fee eventually reaching £6.5 million.
That money allowed Burley to add to his squad more significantly than in previous years. In came John McGreal from Tranmere, Jermaine Wright, effectively be Dyer’s midfield replacement, from Crewe and Gary Croft from Blackburn. Later in the season the Dyer money allowed Burley to recruit Marcus Stewart from Huddersfield and then Martijn Reuser on loan from Ajax.
"Naturally, we didn’t want to sell our best players such as Mauricio Taricco, [who joined Tottenham in 1998] and Kieron Dyer, but we didn’t have a backer, somebody that was putting money into the club,” said Burley, now 63 and based back in Ipswich.
"David Sheepshanks and the board ran it very well, we looked at the books every year and we’d seen what the wage bill was and if we needed maybe £1 million or £2 million to balance the books and that’s what we did.
"And if there was any excess it was given to me to try and get other players in for less money and push ahead in the season.”
The play-off semi-finals were games that no Town fan will ever forget, the Blues having been two down after 26 minutes before Marcus Stewart scored two brilliant goals to restore parity ahead of the midweek second leg at Portman Road.
"It is a long season in the Championship, you play a lot of games and then you’ve got a little bit of a wait before you start in the play-offs,” Burley recalled.
"Marcus Stewart got two goals in the away game, that kept us in the tie, that was crucial and I think if we hadn’t have scored that second goal it would really have been an uphill battle. That kept us in the tie.
"We went away from home, we knew it was going to be tough but I think we had plenty of confidence coming back to Portman Road.”
"The home tie, which ended 5-3 after extra time to give the Blues a 7-5, had everything - eight goals, three Town penalties - one missed - and two Bolton red cards.
"I know Sam Allardyce felt aggrieved with the decisions but I’ve looked back at the game and I would say that maybe there was one sending off that was dubious but apart from that I think the referee made the right decisions,” Burley insisted.
"It was a case of handling the nerves. We went behind and we battled back, missed a penalty and we scored penalties and they had players sent off and I think they lost a bit of discipline and I think that cost them.
"I was always a believer, and the players showed that, that you’ve got to have a disciplined team. We always had that at Portman Road and I think won us the game. We kept our discipline, Bolton didn’t and we went through on merit.”
Town had 12 days to wait for the final and Burley had a number of injury worries to contend with. John McGreal had missed the previous six weeks due to an ankle injury, David Johnson had carried knocks during the semi-finals - and would pick up a calf problem in training ahead of the final which made him a doubt right up to kick-off – while James Scowcroft was definitely out having torn a hamstring.
"That’s football, you’ve got to look at the positives rather than the negatives,” Burley said. "It’s easier to say as a manager that it’s because I’ve had injuries [if results don’t go your way]. We were always positive and we had a good squad of players.
"We were all brought up in those three or four years together, most of the team had been together for a long time, so there was always a great spirit amongst us.
"I think the experience of the years before, missing out in the play-offs, stood us in good stead so even though we had a few knocks and a few doubts, we were very positive going into the final.”
McGreal was declared fit and Johnson also started but Burley still had other decisions to make regarding his starting XI.
Many fans had expected Reuser to get the nod in place of Scowcroft but in the end Jermaine Wright came into the midfield. At right wing-back Fabian Wilnis played the first leg of the semi-final but Croft the second and it was the ex-Blackburn man who kept the shirt for Wembley.