Twenty years ago today the Blues beat Barnsley 4-2 in the First Division play-off final at Wembley and TWTD caught up with skipper Matt Holland to hear his memories of that great day.
Town went into 1999/00 having been beaten in the play-off semi-finals for three successive years.
Having been the early season pace-setters, they eventually finished third behind champions Charlton and Manchester City in a tight race with the second automatic promotion spot in contention on the final day when the Blues hosted Walsall and Joe Royle’s City were at Blackburn Rovers.
Town needed to win and hope Rovers defeated City and for a while it looked like those results might be on the cards before Royle’s men recovered to win 4-1 to claim second spot, while two David Johnson goals saw the Blues to a 2-0 win.
"City were behind and we were ahead on the last day, so for a few minutes it looked like we were going up automatically,” recalled Holland, who will join his team-mates on a Zoom call organised by striker Marcus Stewart later today to celebrate the anniversary.
"But we don’t like to do things easily, do we? We have to make things difficult for ourselves, a bit like the final as well, going behind in that. It wouldn’t have been Ipswich if we’d done it simply.”
And so it was the play-offs for a fourth successive year with Bolton the opponents in the semi-final for the second year in a row.
The Trotters were eventually vanquished 7-5 on aggregate after two never-to-be-forgotten ties to set up a final at Wembley against Barnsley, who had finished fourth, five points behind the Blues and who had comfortably defeated Birmingham in their semi-final.
"I don’t think we had any fears about the play-offs that year because we’d been behind so many times in games as well,” Holland said.
"I think that was the thing we found that season, being 2-0 down at Bolton in the first game, I don’t think we were ever unduly affected by being behind in matches.
"And I think once we got to the final because we’d been to the play-offs three times and not made it to a final, it wasn’t a feeling that it was definitely going to be our year, but there was definitely something. You feel ‘This is us, this is our turn’.
"I think there was that about it and I think the team had been together a few years as well. George Burley had made one or two additions in the summer, Marcus Stewart came in in January as well tipped us over the line.
"George had been building a squad anyway and there were a lot of players in that dressing room who had been around the block a bit and seen it all. I just think it was the right time, it just felt like it was going to be our time.”
Going into the game the Blues had more than a few injury concerns. James Scowcroft, the Player of the Year that season, was ruled out completely with a torn hamstring, while David Johnson, Tony Mowbray and John McGreal, who had missed both legs of the semi-final, were doubts.
"Scowy obviously missed out, which was a big blow, he’d had a great season. That was a big one for us.
"I think the squad that we had, we felt pretty comfortable really. I think we had a decent squad with the additions that we’d made. Marcus coming in made a big difference to us up top.”
In the end all three were passed fit and Town travelled to London on the Saturday ahead of the bank holiday game with manager George Burley trying to keep the atmosphere as much like a regular match as possible.
"I remember George in the build-up saying that he wanted things to be as normal as possible, he didn’t want to change too much,” Holland said.
"He didn’t want to change the way we trained, he didn’t want to change anything about what we’d been doing all season, didn’t want to make it a bigger thing than it needed to be really because obviously it was a massive day, a massive occasion.
"I think he wanted to keep it as level as possible and not be affected by the magnitude of the game really.
"I think we might have gone two days in advance, it’s in my head staying in the hotel two nights before the game rather than just one, which was slightly different rather than just one night’s build-up.
"I think there was an air of confidence but obviously a few nerves as well, it was a big day, a big occasion and we’d been knocking on the door for a few years as well.
"I guess the pressure on us was there a bit and the fact that we’d finished third and finished quite a bit ahead of Barnsley in the league, there was a bit of pressure on us as favourites going into the game.”
Holland says the journey to Wembley on the coach brought home the significance of the occasion: "You’re looking for the twin towers at that stage, you know you’re getting closer, you start seeing supporters milling around, you see the twin towers, you drive under the ground into the stadium.
"Then it becomes real. In the hotel, you’re eating breakfast, you know the game’s coming but the moment you start arriving and you see the fans and you feel the atmosphere, that’s when you know it’s real and I think that’s when it hits you.
"It was a bit of a walk at Wembley from the tunnel to the pitch to take a look at it. I guess that’s when it hit home that it was a big occasion.”