Guppy's 'Magical' Foxes Memories
The Winchester-born winger, who had already played for Martin O'Neill at Wycombe Wanderers, joined the Foxes in 1997 and quickly became an essential part of the Northern Irishman's side.
One season after being beaten in last minute of the the 1999 final by Tottenham Hotspur, all that stood between Leicester and a second attempt in as many seasons was a two-legged tie with Aston Villa.
John Gregory's men were favourites, especially considering an injury crisis which has engulfed City in early 2000, but O'Neill's men nonetheless secured a goalless draw in the first left at Villa Park.
"This cup run was quite unusual for a number of reasons really," Guppy explains, speaking in Orlando, Florida. "Injuries happen at any club, but it seemed to really come all at once that year.
"Like every cup run, as you start ticking off the games, you start to get more and more excited. Everyone had been there before already, they knew what it was all about, they knew what was at stake.
"It was fantastic to be part of that and start to build a bit of momentum. The Villa game feels very special to all of us. We were up against it with injuries when we went to Villa Park.
"I feel like I’m crying it in here, but I was having injections before each game. I wasn’t actually taking part in the warm-ups because my knee would balloon up too much, but it wasn’t just me.
"There were loads of lads who were struggling, and we just had to try and find a way to grind out a result that we could get back to Filbert Street with, something intact, something to chase.
"There’s no one better in the game then Martin at really getting the best out of the players, making them believe, even when they say you’re up against it with injuries, or whatever.
"I think the reason we look back on that game so fondly is because Villa were pretty dismissive of us that night. We ground it out, we really worked hard.
"We didn’t get a lot done in the final third, it really was as a case of: ‘Listen, we’re just going to try and hold on to what we’ve got’.
"There was something quite amazing in that respect, in that result, more than any result in my whole time at Leicester. That night we really had to dig deep for a number of reasons, all over the park.
"Villa, fair play, they threw everything at us, but after the game, there was a few things… the manager and few of their leading players said they really fancied it in the second leg.
"They said things like: ‘Leicester have got to come out their own half’. We thought it was a bit unfair because we weren’t that sort of team. We were pretty gung-ho at times.
"It was just that situations dictated that that is what was going on. It really got us even more galvanised really towards that second leg and everyone was tuned in for that second leg."
A collective desire to shrug off the 'Boring, Boring Leicester' tag given to City by the national newspapers inspired the Foxes to an excellent 1-0 victory at Filbert Street, courtesy of Matt Elliott's header.
"Come the second leg, I was back and I felt like things had improved there, but we still had a makeshift team," Guppy added. "Matty was playing up front that night and thank goodness he did!
"But also, there was a lot going on, but despite all that, with a fantastic manager who really dragged it out of us, and we were ready for Villa that night.
"When there’s a carrot of a cup final at stake… the manager and the coaching staff, people like John Robertson and Steve Walford, they drag you through and make you believe.
"Obviously, on the pitch, the players, the leaders we had on the pitch, we all felt a unity, that night especially, that dragged us through.
"There’s certain memories in your career where you remember, you can see it in your mind’s eye, I can see it now… where the cross came in and then Matty Elliott’s there.
"He’s given one movement to fool the defender and then come across him and then a bullet header in the back of net. I can see it now.
"An absolutely fantastic finish for basically a ‘makeshift’ centre-forward, but Matty was a talented player, obviously a fantastic defender, but on the occasion he played up front, he could play that role.
"That goal, I can still see it, for whatever reason, it’s still in my head, and then obviously the celebration when he’s running back, we’re like: ‘Right, we’ve got something here and we’ve got to try and hold onto it’.
"It was lovely, walking around Filbert Street, the few times we did it. The music’s blaring, Tina Turner’s Simply The Best, they’re the little things you remember.
"It’s fair to say, we did enjoy ourselves back then. We didn’t have the age of the video camera and there was an opportunity to still enjoy yourself.
"You’d maybe mix with the crowd more than maybe the players do today. That’s how it was. It was absolutely fantastic, walking round the pitch, but it was a real feeling of accomplishment.
"It wasn’t like everyone was hitting their stride, we were a patched-up team, a lot of lads struggling, but as the manager always said: ‘You’ve got to find a way to win’. We did that night, which was magical."
First Division Tranmere Rovers, who'd defeated Bolton Wanderers in the semi-finals, awaited Leicester at Wembley in the showpiece final on 27 February, 2000.
City's role had been switched. They were now big favourites to secure a second League Cup success in four seasons, but Guppy and his colleagues were determined to savour the occasion.
"Looking back now, it’s not just yourself, it’s your families," the former winger continued. "My mum and down used to hire a coach, living down in Southampton, all my relatives, and I used to pay for it… no one ever gave me the money… they still owe me the money for the tickets!
"But they all came up on the coach. It was a great day and when you look back now, as time’s gone by, it’s really nice that your parents got to enjoy that moment as well as you.
"Any Wembley final is an amazing experience. Those are the fond memories, those day trips, and trying to win a cup, it’s something that you can look back on and go: ‘Yes, we actually won something’.
"Playing at Wembley, you never get tired of it, especially the old Wembley. When you walk out of the dressing room and you walk up the little incline, out of the tunnel, and then the crowd see you… I think those sort of things you dream of as a kid.
"I know it’s sounds a little bit corny, but you do. You think what must it be like and it’s one of those few moments in life that was every bit as good as you’d hoped it would be."
Guppy's role in the final was simple: to provide deliveries to the likes of Elliott, Emile Heskey, Tony Cottee or Gerry Taggart, who'd be there in the box ready to pounce.
Lightening struck twice for the Foxes, despite former Fox David Kelly's equaliser initially causing concern, as Guppy landed a brace of inch-perfect corners onto the head of Elliott in the area.
He explained: "My part was to get the delivery right, but obviously the boys in the middle, they’ve got to want it more than the opposition and I think Matty showed that day that he wanted it more
"For that first goal, when it went in, was obviously a great feeling after what happened the year before.
"We had scored, whereas against Tottenham, the year before, we hadn’t scored and you always want on that day out Wembley for the supporters and your family to get a goal.
"Then you’re up and running and then everyone enjoys it. Everyone feels like they go to Wembley and they want a goal so everybody can celebrate it and that would have settled us down really nicely.
"I think we were doing pretty well in the game and then Tranmere had the period, it always happens, and they got their goal.
"I remember being a bit shocked to be honest, I’d been reading the script and it wasn’t in there. I thought we were looking quite comfortable.
"Fair play to them, they got themselves back into it, they got the equaliser. There was still plenty of time and it was down to us to put it right and we did with the second.
"Tranmere’s goalkeeper was one that liked to come for crosses. So, I was wary of that and the manager was wary of that, so if you look at that second goal, Tony Cottee went on the ‘keeper.
"He didn’t foul him, but he did just enough. I felt if I hit the area and got the whip on it that Matty would to do the rest.
"But if Tony hadn’t done what he did, I think there’s a chance the ‘keeper comes and grabs that, or at least things could have been different.
"Tony was a massive part of that goal, even though he never touched it. If you watch it again, he did enough to keep him on his line and then obviously Matty Elliott got a great connection.
"He knew the areas that I would be aiming for and he timed it perfectly and obviously that moment when it went in the back of the net, you don’t get enough of those moments in life."
Winning silverware with the Club allowed the players to forge a real bond with the Blue Army in the late 1990s, all inspired by O'Neill, who remains one of the greatest managers in Leicester's history.
"To win at Wembley, it’s fantastic," Guppy said. "Football’s a roller-coaster ride, it really is. "The lows are horrible. When you’re growing up, you may get released, and you get sold, you get dropped… all these emotions that you have to endure throughout your whole career.
"So, when those moments in the sun arrive, you’ve got to enjoy it. There’s no better place really to celebrate a win than on the pitch at Wembley, with your team-mates, your family in the stand, all together.
"One of the funny things actually, coming back after the game, we were caught in a big traffic jam going up the M1, and all around us were Leicester fans because they’re all driving back.
"I think there was one point when some of the lads were going out of the bus and handing beers out to the fans, but that’s all part of it. The full package is just fantastic.
"When you think about the characters that the manager assembled… I think the truth is this: Martin O’Neill was a strong character.
"He’s the strongest out of all of them and, if you look at the players that he recruited, they were very talented, but sometimes would be perceived as being ‘hard to handle’.
"Some managers would shy away from that, whereas he wanted to embrace it, because I think he knew if he could channel it, then we’d be hard to beat at the big moments.
"When you think, the Tranmere game, when they’d be shelling that ball in with the long throw in the final, you’ve got those characters at the back.
"They’re ready to stand up and be counted. I think that became a massive part that was played in Martin's recruitment and that’s why I think things went so well."
20 Years On: Leicester’s League Cup Triumph can be viewed now, for free, on LCFC TV.