As we continue our build-up to Sunday's Carabao Cup final by reflecting on Chelsea's previous successes in the competition, Frank Sinclair talks us through the Blues' 1998 triumph and explains why it was a defining moment in his career.

Frank Sinclair had twice been to England's national stadium following his Chelsea debut in 1991.

There was heartbreak for the Academy graduate on his first visit. Sinclair conceded a penalty as the Blues were comprehensively beaten by Manchester United in the 1994 FA Cup final.

Better was to come three years later as, once again in the FA Cup final, Chelsea defeated Middlesbrough 2-0. Roberto Di Matteo and Sinclair's close friend Eddie Newton struck to make it a Blue day and ensured we claimed our first major piece of silverware in 26 years.

Less than 12 months on from that Wembley outing, Chelsea returned for the League Cup final. Middlesbrough were again the opposition, but the journey to the final had been far from smooth.

The Blues twice needed penalty shootouts to advance; in the first round against Blackburn and following a 2-2 draw away to second-tier Ipswich Town in the quarter-finals.

A mouthwatering two-legged clash with London rivals Arsenal took place in the semis – and the Gunners came away from a tight first leg at Highbury with a 2-1 lead.

However, ahead of the second leg, player-manager Ruud Gullit departed the club. It came as a shock to Chelsea supporters, as did the announcement that Blues striker Gianluca Vialli would take the reins.

‘We were shocked like everyone when Ruud left the club,’ Sinclair explains. ‘That was probably one of the most shocking days in the club's history.

‘But it was quite seamless actually because everybody loved Gianluca. He was a favourite among all the boys in the changing room and we wanted to do our best for him because he was that type of character.

‘That transition to him taking the job was ok. Everybody wanted to do their best for Luca, particularly because we understood how difficult it was to take that role during the season, with all the responsibility that brings.

‘There were so many important games left – including the one against Arsenal – but we were a confident team after winning the FA Cup the year before.'

Gullit's departure remained a seismic shock that reverberated beyond west London. At the time of the Arsenal semi-final, Chelsea sat second in the Premier League and were in the last eight of the Cup Winners Cup.

Just six days after taking charge, Vialli had to prepare his side for the second leg against Arsenal. The Italian inspired a stunning turnaround with Dan Petrescu, Di Matteo, and Hughes all on target during a scintillating performance at the Bridge.

It booked the Blues place at Wembley once again – and Vialli's side were firm favourites to overcome Middlesbrough, who had eliminated Liverpool at the semi-final stage.

‘The mood within our team was good,’ Sinclair says. ‘But the biggest focus the likes of myself, Steve Clarke and Eddie Newton had was that we knew what it was like to lose in a final after 1994.

‘You realise that for cup finals, even though it’s a massive stage, you have to make sure its business as usual. We took that into both finals against Middlesbrough because while it's a special day if do win, it is an awful day if you don’t.’

And, in the mind of Sinclair, the new man in the Stamford Bridge dugout felt the weight of preparing a team for a Wembley final.

‘Building into the game we knew Luca was really nervous. He was just that type of character. It’s surprising for some considering what he achieved in the game and the levels he played, but that is just how he was.

‘He would be nervous for any game. If we were facing a team from League Two in the first round, he still would have been that way. It was just him. You could see going into that game, his body language was tense and he wasn’t great at hiding it.

‘But generally, as a team, we were very relaxed. We were confident we had the ability, but we also knew we were playing a better Middlesbrough team than in the FA Cup final. They had just signed Paul Gascoigne, who we knew could impact the game.

‘They had better players and we knew it would be a big challenge. We knew they’d have an edge, wanting revenge for the year before. We had to match that.’

Like many finals down the years, it proved a cagey affair. Both sides were cautious to overcommit in attack, with Sinclair part of a disciplined, well-drilled Chelsea back three alongside Frenchmen Frank Leboeuf and fellow Academy graduate Michael Duberry.

Midway through the second half with the game goalless, Boro introduced Gascoigne and the game started to open up. Vialli responded with tactical tweaks of his own, meanwhile, Sinclair was struggling with an injury.

‘Steve Clarke came on midway through the second half and I went to the right wing-back where Dan (Petrescu) had been.

‘Obviously, it was too late to say anything about the injury by then so I just battled through. I had a little bit of pain but just got through it, which is easier when you’re trying to win a game.

‘It was a draining day as it was quite warm as well. The size of the pitch at Wembley is always going to sap your legs but as far as I was concerned, it was the same for everybody.

'You could tell by the pace of the game, how much it had slowed down in the latter stages, you knew everyone was feeling it.

‘My mindset was more defensive and I was thinking 'just make sure they don’t score'. And that was why Gianluca made the switch, to keep it tight.

'To bring on someone with the experience of Steve Clarke, we were probably first and foremost looking to get the clean sheet, maybe gamble on winning it on penalties.’

Both teams had chances but at 90 minutes the score was 0-0 and the final went to extra-time. Unlike the year prior, Chelsea would have to dig in for another 30 minutes to bring back the silverware.

What followed in the 95th minute will never be forgotten by Frank or the thousands of Blues at Wembley that day. After nicking the ball inside the Middlesbrough half, Sinclair drove forward and played a pass out wide to Dennis Wise.

Sinclair then opted to move into the penalty area. 'I don’t know where I got the energy from to get forward into the box,' he remembers. ‘I was very fatigued at the time.

‘Playing with Wisey for a number of years, I almost pictured where he was going to put the ball before it actually happened. There were so many times where the ball got played to Wisey and it looked like it was going off the pitch, but he would get there and have the ability to still get a decent cross in.

‘I was the only one in the box reacting to it thinking ‘he is going to get a good cross in’. I got myself into the box, he wrapped his foot around the ball and picked me out brilliantly.

‘I then found the perfect header, putting it where it was difficult for the keeper to save. It was a eureka moment for myself.’

Considering Sinclair stood at 5ft 8ins, the header was far from simple, but the defender managed to leap high and get above the ball to knock it back into the ground.

Middlesbrough goalkeeper Mark Schwarzer had no time to react - there was too much power on the header – and Sinclair, barely able to continue running, collapsed to the turf in celebration. He was quickly mobbed by his teammates.

‘To score at Wembley, every kid growing up playing football dreams of that. As a kid all you dream of is number one, playing for your country, and two, you want to score at Wembley.’

Despite the delirium, the game wasn’t done and the injury Sinclair had started to feel in the second half was now putting him under strain. Middlesbrough had time to salvage something and possibly force a first-ever final penalty shootout.

But with 13 minutes remaining, Di Matteo again proved to have the magic touch in a cup final. Our No.16 repeated his heroics of the FA Cup final the year before - when he had scored the fastest goal in Wembley history – to finish off fro from Zola’s low corner to seal the deal.

A second blue pile-on in the corner followed while Vialli was suddenly the coolest man in Wembley, celebrating calmly on the touchline. The League Cup was coming back to the Bridge for the first time since 1965.

Frank recalls: ‘The (tactical) switch worked really well, it gave us momentum and then I got the goal. Robbie got the second to finish Middlesbrough off and from that point on we knew it was ours.

‘Like most finals, it was pure relief at the end. It was a great day because like I said we knew how bad a final can be if you lose it.

‘Honestly, the celebrations were probably a little bit limited because I think we all knew in the back of our minds we still had business to take care of that season, particularly in the Cup Winners Cup.

‘Games were coming thick and fast every week, so we had a quiet celebration that night, then put it to bed and went back to business.’

The victory at Wembley turned out to be Frank’s final game for the Blues, as his efforts to ensure Chelsea claimed the League Cup over 120 minutes resulted in his groin injury becoming significant.

‘I didn’t think it was that bad at the time,' he says. 'Obviously, at the time, I didn’t know it would be my last game for the club.

‘My focus was on trying to get fit and be a part of the rest of the season if I could get back. But it wasn’t to be. Unfortunately, my groin tear was so bad that I missed the rest of the season.’

Frank joined Leicester City the following summer after 218 games for Chelsea. Having been with the club he loved since 11 years of age, leaving the King's Road was never going to be easy. But what a way to bow out.

‘If I’d have ever been asked, ‘How would you like to sign off from Chelsea?’ I would have said to score in a cup final!

‘To also score a really important goal in the Cup Winners Cup quarter-final as well in the previous game, it was a dream way for me to cap my time at the club.

‘This game has to be right up there when looking at my career highlights; representing my country Jamaica at a World Cup final and winning the FA Cup were also right up there. But that final and scoring are definitely in the top three, for sure.’

Although Sinclair was out injured, the Blues went on to claim more silverware a couple of months later, with a 1-0 win over Stuttgart in Stockholm securing the European Cup Winners Cup.

Sinclair made five appearances in Europe that season, with his goal against Real Betis crucial in the last eight. His roles in our trophy successes in both 1997 and 1998 were hugely important, and his commitment to the club could never be questioned.

‘All I knew was Chelsea, it was embedded in me as a fan,' he says. 'The club had a massive transition from when I first joined as a kid and a lot of people have played a part in that.

‘To look back at where it was, what Chelsea became in the nineties, and where it is now, it is incredible really.'