Taggart and his team-mates endured 90th-minute heartbreak against Tottenham Hotspur in the capital in 1999, but they were back beneath the old Twin Towers at Wembley just 12 months later.
Alongside either Matt Elliott or Steve Walsh in the heart of Leicester's defence, Taggart typified the determined grit and passion which epitomised Martin O'Neill's odds-defying Foxes in the late 1990s.
Reflecting back on that awful experience against Spurs, the 51-capped Northern Irishman told LCFC TV: "We thought we’d lost our opportunity of lifting a trophy at Wembley.
"When we analysed the final after we’d come off the pitch, we realised that was probably a game we should have won. We matched Tottenham.
"They were obviously the favourites in the game, but I thought we more than matched them. You’d have thought, with Justin Edinburgh sent off, that would have given us an advantage as well.
"Unfortunately, we couldn’t take advantage of the advantage, and in the end, Tottenham deservedly won it with a counter-attacking goal which we just weren’t able to cut off, so it was very disappointing."
Taggart in action during the League Cup Final against Spurs.
City regrouped the following season, eventually securing a fourth consecutive top-10 finish in the Premier League, while Taggart himself scooped the Club's Player of the Season prize.
The crowning moment, though, undoubtedly came on 27 February, 2000 as O'Neill marked his final season in charge of the Foxes with his second League Cup triumph in three seasons at Filbert Street.
"We were away at Crystal Palace for the first game and we had a pretty strong team out because I’m sure Martin was not happy with getting beat in the final," Taggart remembered.
"He wanted to give himself the best chance of his team getting back to the final the year after. So, that’s probably why you saw a pretty strong team going out that evening at Selhurst Park."
After dispatching Palace, duly defeated Grimsby Town, Leeds United and Fulham before a fraught two-legged semi-final clash with Midlands rivals Aston Villa.
O'Neill was forced to be pragmatic in the away first leg, largely due to an injury crisis which engulfed his Leicester squad, but the visitors nonetheless left Birmingham with a 0-0 stalemate.
"What can I say about Villa Park?" Taggart added. "It’s probably one of the worst games I’ve ever played in basically, as regards to shots on goal for us.
"I know we were missing some big players, some key players were out missing that night. Even with a full-strength Leicester City side, that would have been a difficult place to go and try and get a result.
"On that occasion, I think the best outcome we could have was a 0-0 draw, or a 1-1 draw, a score draw, an away goal, because of course, back then, away goals counted.
"Thankfully, we didn’t concede... we didn’t look like scoring to be honest with you, so pretty early on in that game we’re thinking: ‘If we come out with a 0-0, we’ve swam the channel’. And that was the case."
Winning the semi-final, again for me, stirs more emotion than the final itself, more elation should I say.Gerry Taggart LCFC TV
The deciding encounter between the two teams came just a week later and the Filbert Street crowd ended the night by toasting the prospect of yet another trip to Wembley for the Foxes.
"It was another tense night, I have to say, it really was!" Gerry continued. "Again, [it was] not a great game, but there was a few key moments in the game.
"Obviously, the first one that everyone will remember was Matty’s headed goal. He was actually running backwards, when the ball comes into the box, he’s running backwards, he’s headed the ball in the net.
"He’s celebrating on the same move, while he’s still running backwards. So, how he’s pulled that off, a man of his size, I’ll never know, but fair play to him!
"Obviously, it turned out to be the winning goal, but in between all that, I remember Tim Flowers pulling off an absolute cracker of a save, from Steve Stone it was.
"That save proved to be probably the last bit of serious goalmouth action and we just saw the game out. Again, [in] the last 10 minutes, the Cat (Flowers) pulls off a great save.
"We go on to just see the game out; grind it down, run the clock down whenever possible, get in the corners, do whatever it takes, make the game look ugly and, again, that’s exactly what we did.
"Winning the semi-final, again for me, stirs more emotion than the final itself, more elation should I say. I think there’s some scenes afterwards, there’s probably some video footage as well, in the dressing room, and I’ve got this photograph of me in all my glory… me in all my finery, just my shorts on, basically, and my ankle strappings, popping a bottle of champagne.
Inside Filbert Street's dressing room
Taggart and his team-mates celebrate booking their spot at Wembley.
"That was as good as it gets for me, by the way, physique-wise anyway! When I talk about elation, I think after that game, it’s more about reaching the final, going back to Wembley.
"We’re not under any illusion that the cup’s in the bag, we’re going to win it this time. Yes, again, you talk about momentum, belief… we had that in abundance. But it was just about getting back to a final."
Smells or sounds can play a big part in the formation of memories - and the tones of Labi Siffre's Something Inside So Strong is something which Taggart associates with the big moments at Leicester.
After listening to that on the bus journey up Wembley Way, Elliott was the hero for the Foxes, nodding home two Steve Guppy corners to seal a 2-1 win for O'Neill's men in the capital.
"Walshy (Walsh) used to stick on his favourite song, going up Wembley Way, which was Labi Siffre’s 'Something Inside So Strong' and so he’d put that on!" he added.
"I think, in relation to the build-up, I don’t think there was much different to be honest with you, the focus was on winning the game: ‘We have to win this game’.
"As I said, it probably played on our mind slightly because, with the amount of chances we created throughout that game, Tranmere obviously going down to 10 men, I just thought, we made hard work of it.
"It could have been a lot easier, it could have been a lot more enjoyable for us, but at the end of the day, we got the result that we needed to get and everything else after that was a blur!
"When the ref’s whistle went, it was more relief than elation. I was just relieved to have it over and done with, that we’d finally [won] again, it was my first cup win.
"I’d lost a final, I’d now won one, we’d won one at Wembley. The first one against Middlesbrough was at Hillsborough, so there was a bit of talk around that, winning a cup final at Wembley.
"But I just remember seeing Neil Lennon and the pair of us just embraced and the pair of just said: ‘We’ve done it! We’ve done it! We’ve done it, Lenny!’
"And we both fell to the floor and we were on the floor for about five or 10 seconds, rolling around like two little babies, and obviously it’s a moment you’ll never forget.
When I came to Leicester and Martin O’Neill was the manager, I realised that playing football wasn’t enough – it was about winning. The rest is history.Gerry Taggart LCFC TV
"You’ll never forget that as a footballer, winning a cup final at Wembley, but to share that moment with someone you’ve known practically all your life was also a special moment as well.
"We come to the moment we’ve all been waiting for, going up to receive the trophy. It’s something every kid in the country grows up watching, where you just watch the players going up.
"As a young kid, not only do you watch it, but there are times when we actually think about it and think: ‘I wonder if I will be able to do that one day’.
"It’s definitely something that runs through your head, so standing there waiting to be called forward to go up and receive the trophy was when I started really getting excited, I have to say.
"Just the anticipation, the waiting, we’re all going around shaking hands, obviously, with the opposition, with all our own staff, and then just waiting to go up the stairs was probably the most enjoyable bit for me.
"I was fourth in line, so I think, again, Lenny and Sav (Robbie Savage) shuffled their way forward in front of me, obviously!
"Matt was the skipper, and he was the hero of the day, so it was befitting that not only was he skipper, but he was the hero, and he got to lift the trophy.
"Again, it was almost like waiting in queue to get your school dinners at lunchtime when you were a kid! There’s a few people in front and you’re saying: ‘Hurry up, hurry up! I want my turn!’
"So, it was a bit like that. Again, the anticipation, what are you going to do when you lift the trophy? Are you going to kiss it? Are you going to turn to the fans and wave the trophy at them?
O'Neill jumps for joy on the Wembley sidelines.
"Yes, it was all that running through your mind and I think duly obliged by doing all of the above, so yes, I tried to take full advantage of that moment and not trying to let it go by me.
"That’s a moment, lifting the trophy, but unfortunately because I’m in fourth place, you never get to see me actually lifting it. Well, I’m sure there’s a clip somewhere, but it’s a moment that I won’t forget.
"It’s then when it sinks in, as an individual, well it did for me anyway, that you’ve achieved something really big here and everyone’s turning out to celebrate that with you, so that was a great moment.
"I suppose winning, success, it was something I always set out to achieve as a professional footballer. I think early on in my career, it was to play for as long as humanly possible.
"I love playing football, but when I came to Leicester, I realised that playing football wasn’t enough.
"When I came to Leicester and Martin O’Neill was the manager, I realised that playing football wasn’t enough – it was about winning. The rest is history."
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