Born and raised in the city, joining his hometown team at the age of nine and rising through the youth ranks at Leicester, Heskey knew more than most what the Club was all about.
So, naturally, it was an extra special day when he was part of the Leicester City side that lifted the League Cup trophy in 1997.
Had it not been for Heskey’s equalising goal in the final minute of extra-time, which took the contest to a replay, Middlesbrough would have had their name on the trophy.
As it was, following that stalemate at Wembley, a 1-0 victory at Hillsborough saw Martin O’Neill’s side win the competition for the first time since 1964.
But then, having tasted defeat in the 1999 final against Tottenham Hotspur, thanks to a last-gasp Allan Nielsen winner, Heskey and his team-mates were hungry to go one better and do it at Wembley.
“I remember coming up into the Premier League, it was odds-on that we were going to be relegated again,” Heskey said, recalling the 1996/97 season.
The Foxes forward was on the losing side against Spurs in 1999.
“We were known a little bit as a yo-yo team before I got into the side; going up, coming back down, going up through the play-offs...
“But then to go and do what we did – finish in the top half of the league and go to the League Cup Final – was wonderful. But we wanted more of that.
“In the second year, we fell down at the first hurdle (losing against Grimsby Town in Round 3), but then, after that, we decided that we were going to make the League Cup our own.
“That’s what we did. We didn’t put all our eggs in one basket, but we knew what we were capable of doing and we went for that.
“We never really spoke about it or anything like that, but I think it was just a collective thing: ‘This is our chance to go to Wembley’.
“‘Do we have a chance of winning the league? Possibly not, well, definitely not, but what’s the next big thing?’ The cups: the FA Cup, the League Cup.
“Generally, back then, a lot of the bigger teams played their second-string teams in the League Cup, so again, it was our opportunity.
“We were happy to go anywhere and play, whether they had their best XI out, we knew that we were capable of winning anyway.
“But it made it a little bit easier for us when, generally, the bigger teams were out by the first rounds that they were in it.”
City saw off Crystal Palace and avenged the previous defeat to Grimsby Town, then beat an up-and-coming Leeds United side on penalties, before a remarkable quarter-final victory over Fulham, in which Leicester progressed after extra-time, having been two goals down with five minutes to go.
Looking back now, I’m thinking: ‘How did I get through all those games?!’ Ninety minutes, extra-time sometimes, and it would’ve been tough, but the love of the game, you just don’t overthink things.Emile Heskey LCFC TV
“The cup run as a whole was just a lot of games,” Heskey continued. “I remember playing in replays and then having to play a league game, then playing another replay.
“It was just back to back to back to back games! Being a young lad, you just loved it, playing in those games. ‘We’ve got another game? Cool, when is it?!’
“Looking back now, I’m thinking how did I get through all those games?!
“Ninety minutes, extra-time sometimes, and it would’ve been tough, but the love of the game, you just don’t overthink things, I just remember playing a lot of games.
“At that time, Leeds were a very strong team, a very, good team. Some great players at that time: Jonathan Woodgate, Michael Bridges, who I played in the national team with, David Batty.
“But we had a good core base about us and there were certain teams that we had their number and I think Leeds were one of those as well and we drew 0-0, but won on penalties, so it was good.
“Walshy (Steve Walsh) typifies what Leicester’s about; never-say-die, never give up, putting everything in it.
“He’d be disappointed with giving away the opportunity for Fulham to go 2-0 up, but then with him, being the one setting up Marshy (Ian Marshall) to score, then being the one to score.
City fans at 2000 League Cup Final
The 2000 final was City's third visit to Wembley in four seasons.
“I played with Walshy and I’d watched him from a young age.
“I joined Leicester at nine, watched him all the way through there and then he came to a next era of playing with me, and being one of the best players there as well.
“He’s the one that basically puts his heart into everything. Playing up front as well, you’ve got to remember. I watched him in a play-off final against Derby, he scored the goal to go up to the Premier League.
“So, he typifies Leicester and he’ll be disappointed that he gave away that opportunity for Fulham to go 2-0 up, but again, to fight back, 85th and then 87th minute, to come back to 2-2, was phenomenal.”
The semi-final had fewer goals, but was similarly tense, with the two-legged affair against Aston Villa settled by a single goal from centre-back Matt Elliott, scored in the second leg at Filbert Street.
Heskey added: “Heading into it, we were underdogs. They were the big side in the Midlands at that time.
“I’d played against them from a youth level and was always getting beat, but again, you come up against teams and you have their number.
“We were never in awe of them, even though they were a huge team, a huge squad, and we went into that game and we rode our luck a little bit at times.
“But we always knew that we were capable of winning that game.
Back then, it wasn’t a done thing to be playing out and passing the ball. He (Matt Elliott) was brilliant on the ball, one of the first ones I saw. So, to go up front was normal for him, holding the ball up, bringing other people in.Emile Heskey LCFC TV
“We were confident in our group of lads. I remember Matty [Elliott] played up front with me, we were struggling actually for players, but we formed a bit of a partnership.
“I think it was Big Ron [Atkinson] who said something along the lines of: ‘Square pegs, round holes’. I think that spurred Matty on a little bit! He was like that.
“He had immense ability, for a big lad, and being a centre-back as well. Back then, it wasn’t a done thing to be playing out and passing the ball.
“He was brilliant on the ball, one of the first ones I saw. So, to go up front was normal for him, holding the ball up, bringing other people in.
“I remember the ball coming across and seeing Matty and thinking: ‘He’s not heading that in, he’ll have to just bring it down or something’.
“He’s falling away from the goal, with big Ugo Ehiogu on him, and he got enough to head it back, past David James, who was an England goalkeeper at the time as well, so a phenomenal header.
“But we always knew we had the capability of winning that game. We were very strong against Villa and that showed that night.”
The showpiece event, against Tranmere Rovers, proved to be Heskey’s penultimate involvement in a Leicester shirt, as he made an £11M move to Liverpool two weeks after City’s Wembley triumph.
Emile scored a late equaliser against Middlesbrough at Wembley Stadium to send the 1997 final to a replay.
He remembered: “I’ll always remember the trips to Wembley in the sense that you see so many fans! Wembley Way, driving towards it, all you see is blue, you’re like: ‘Wow’.
“My parents are there and my grandparents are there, to come and watch, and there’s so many fans outside beforehand. You have to savour that atmosphere, going to it.
“It’s hard to say, but I believe back then, it was a lot more passionate, when you’re actually coming towards a game, because you can see all the fans and stuff like that. Being in and around them was great.
“To get to a final is not easy. We’d been through it. We’d been through replays, we’d been through penalties, we were down and out against Fulham, and then came back from that, so you have to be wary of that.
“They (Tranmere) had a long throw that we were aware of, but the likes of Matty, Tags (Gerry Taggart), Walshy, players like that, you have to deal with it.
“So, we were aware of it, but again, confident that we could win the game. We made it tough for ourselves, especially conceding the goal that we did, after going 1-0 up, [with] Matty’s great header.
“He likes those headers, coming from nowhere and arching his back and powering it past the goalkeeper, but I think Clint Hill got sent off and then Matty rose again with a header.
“I’m sure Matty’s dad put a bet on him to score in the final, so a good day all round. Yes, I wish I’d have done that!
I was a ball boy at Swindon in the play-offs, so it was huge to actually be doing it yourself and creating a little bit of history alongside that history as well.Emile Heskey LCFC TV
“My immediate emotion was retribution to be honest with you because of Tottenham. In my eyes, we should have won that one.
“Again, getting to cup finals, you always want to win. We’d done four Wembley appearances in five years, so we always wanted to win.
“That was just a great relief that we’d gone there again, and we’d won it this time.
“I didn’t realise that it was the first time we won a cup final at Wembley. When you look back, we drew the first League Cup one, then we won at Hillsborough, so yes, it was great memories.”
Heskey admits he recalls his City career fondly as a whole and in particular looks back fondly on being a young player coming through to play alongside the legends he had grown up supporting.
He said: “I obviously went and watched Leicester play as a kid. I was a ball boy at Swindon in the play-offs, so it was huge to actually be doing it yourself and creating history alongside that history as well.
“It’s crazy isn’t it? When you look at it that way, I didn’t even really think about it that way. What would I have been? About a 12 or 13-year-old kid?
“Then you fast forward four years, I’m playing in the play-off final against Crystal Palace, where Stevie Claridge scored.
“I never really thought about it to be honest with you! Everything just kind of happened very quickly.
Heskey celebrates with strike-partner Steve Claridge after his last minute equaliser in the 1997 final.
“If you look at it, I made my official debut at 17, but I played in the pre-season at 16, three years prior I was chasing balls, giving them back to players at Wembley!
“So, it’s crazy to think of it that way, to be honest.”
The former England international would go on to play for his country at two World Cups and two European Championships, as well as lifting a cup treble in one single season with Liverpool, but his first League Cup medal with Leicester is one he cherishes.
He continued: “Sitting with the lads, having a discussion about winning the game and showing our medals and everything was just phenomenal.
“Then getting back to Sketchley Grange, sitting down and watching everyone party, it was great.
“Everyone just loved a drink and a party with music and dancing, and they were just enjoying themselves, so it wasn’t wild, like anything crazy going on, but we knew how to party.
“My first League Cup win ranks up there as one of the best, because coming from Leicester and not being fancied, odds against you, then to go and actually win it.
“I would have been about 19 at the time, so winning that for your hometown club is immense, so that would be one of my favoured moments.
“But not just being a flash in the pan, and being able to go on and win it again, after losing in the final, which I thought we should have won, but after losing in the final, was great.”
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