The 1999/2000 season was one of the most memorable for Chelsea, even if our cup runs did eclipse our fortunes in the Premiership.

Under the stewardship of Gianluca Vialli – managing the club for what would be his last full season at Chelsea – the Blues were expected to build on the third place finish of the last campaign, however the eminent Italian was unable to juggle league and cup campaigns and possibly ended up suffering because of it.

Vialli had spent big in the summer, or what was considered big back in the late nineties, shelling out £10m on England striker Chris Sutton and just over £3m on iconic French midfielder Didier Deschamps. Jes Hogh and Mario Melchiot also joined the club, albeit for little outlay. Also coming in to the squad over the course of the season were Gabrielle Ambrosetti, Carlo Cudicini, Sam Dalla Bona, Emerson Thome, and George Weah.

World Cup winner Deschamps had been brought in to add a touch of culture and vision to the midfield, while Sutton was added to the squad to bring goals which the Blues had lacked in previous campaigns. But it didn’t quite work out as planned, with Deschamps underwhelming and eventually moving on after this season, and Sutton misfiring and misfiring over and over again until following the Frenchman out of the exit door at the Bridge. True heroes of the 1999/2000 season were the free-scoring Gus Poyet, who netted 18 goals in all competitions from midfield, Tore Andre Flo who led the line while Sutton floundered, and Dennis Wise – or ‘Oh’ Dennis Wise as he came to be known following a famous goal – who won the Player of the Season award.

The Blues flew out of the blocks in the first game of the season against the hapless Sunderland. Poyet bagged two, including an eye-catching volley following fantastic link-up play with Gianfranco Zola who netted himself. Flo also got on the scoresheet after coming on for Sutton in the second-half. The benchmark had been set.

A draw with Leicester – featuring an own-goal from ex-Blue and infamous shorts-dropper Frank Sinclair – brought us back down to Earth, but we remained unbeaten until mid-September when we lost to newly-promoted Watford.

No matter. The squad galvanised and beat Middlesbrough in the next league game before the visit of Manchester United to the Bridge. It almost feels unnecessary to write what happened next, but just in case it’s not ingrained in your collective memory’s – and because it’s nice to reminisce – treble-winning United were absolutely thumped 5-0 by Chelsea. And, get this, even Chris Sutton scored.

Poyet opened the scoring within seconds of the whistle, putting the Blues in the driving seat immediately. Sutton added a second before Wise baited Nicky Butt into a sending-off offence, and United found themselves behind in terms of goals and personnel. Poyet added his second and Chelsea’s third after the break, followed by an own-goal from Henning Berg and a clincher by substitute Jody Morris. Stamford Bridge erupted at the final whistle, and a message of intent rang out across the Premiership.

However, the inconsistency that plagued Chelsea in previous seasons and prevented any serious title challenge again reared its head and made a mockery of the display against the reigning champions. Three defeats immediately followed the United win, with Liverpool, Arsenal – featuring THAT hat-trick from Nwankwo Kanu – and Derby County picking up maximum points against us. Two draws followed as the rain began to pour, and then a reprieve with a tight 1-0 win over Bradford City before Sunderland gained payback for their opening-day thrashing by inflicting a 4-1 win over us at the Stadium of Light.

Another defeat – this time at the hands of Leeds – was added to really rub the poor run of form in – but a sixteen-game unbeaten streak followed and kick-started Chelsea’s faltering title challenge. Sheffield Wednesday would ultimately end the run with a 1-0 win, albeit against a weakened Blues side with one eye on a Champions-League clash against Barcelona which was looming on the horizon. Manchester United had all but wrapped up the title and Chelsea’s inconsistency was costing the Blues dear.

Vialli led Chelsea through the final five games of the season with a pattern of results which summed up the league campaign in general: DLWLW. Chelsea finished fifth in the table, a gigantic 26 points behind the side they humbled in the first-half of the season, Manchester United, and four points off Leeds United in third, who would play in the Champions League next season.

It was disappointment for the Blues, who had gained a taste of Europe’s elite competition during the 1999/2000 season. Having finished third last season, Chelsea had to negotiate a qualifying round to make it into the first group stages. They beat Latvians Skonto Riga over two legs and took their place in Group H along with Hertha Berlin, Galatasaray, and European giants AC Milan.

The Italians were first up and visited the Bridge. In the end, they escaped feeling lucky to leave with a point. Chelsea impressed, but lacked a cutting edge, even with Sutton on the bench. A trip to Berlin followed, as did a defeat as the German side won 2-1 in front of their own fans. If Chelsea were to stand any chance of qualifying for the next group stage – that’s right, there were two in 1999/2000 – a win against Turkish side Galatasaray was imperative. It was also no problem, with ‘Super’ Dan Petrescu netting for a 1-0 win.

A trip to the intimidating Ali Sami Yen stadium – or ‘Hell’ to you and I – followed, with the Turks looking for revenge amidst an extremely hostile reception. However, the catcalls and whistles were silenced after 90 minutes, as Chelsea inflicted a memorable 5-0 win over their less-than accommodating hosts. Flo bagged a brace, Zola netted, Wise added a fourth, and the ‘Italian Ryan Giggs’ Gabrielle Ambrosetti put the icing on the cake with a late fifth. The San Siro was next.

Chelsea, needing at least four points to qualify from Group after Hertha Berlin beat Milan, knew that they could not come away from Italy empty-handed. The Blues held the Rossoneri for 74 minutes, but a header from Oliver Bierhoff opened the scoring and left Chelsea’s European hopes in tatters. Vialli responded by throwing Roberto di Matteo on for Gus Poyet and it didn’t take long for the Italian to make an impact. Lofting a diagonal through-ball forward, di Matteo pumped the ball into the danger zone and bamboozled the Milan defence. Wise latched on to it and slipped the ball under Milan ‘keeper Christian Abbiati. It was a f*****g great goal, and spawned a memorable terrace chant as well as winning a valuable point for the Blues. A 2-0 win over Hertha Berlin in the final group game saw Chelsea top the group in their debut Champions League season.

The second group stage threw up some more prestigious European names, as Vialli’s side were drawn with Feyenoord, Lazio and Marseille. A win, draw and defeat respectively started off the second phase, but subsequent wins against the French and Dutch sides secured Chelsea’s place in the quarter-finals, even before Lazio became the first side to come away from Stamford Bridge with a European competition win.

Barcelona were the reward for Chelsea’s endeavours, and although games against the Catalan giants are almost annual these days, the visit of the tournament favourites was a momentous occasion in 1999/2000. A thrilling performance followed as the Blues refused to bow down to the Spaniards, and a team consisting of the likes of Emerson Thome, Celestine Babayaro and Jody Morris ran out 3-1 winners against the side boasting the talents of Luis Figo, Patrick Kluivert and Rivaldo. Zola and Flo – who netted two – scored inside eight frantic first half minutes to put the Blues 3-0 up, but Figo’s consolation in the second-half was to prove costly.

Barca went 2-0 up in the second-leg before Flo pulled one back, but three subsequent goals from the home side put paid to Chelsea’s Champions League hopes. We may not have won the trophy, but we certainly gained massive respect from the European footballing fraternity until we met the attacking might of Barcelona.

We did fare better in domestic cup action however, although the League Cup third-round exit at home to Huddersfield Town will quickly be glossed over.

At the same stage in the FA Cup, Chelsea started the competition as they would finish it. A 6-1 win over Hull City featured a Poyet hat-trick and a rare Sutton strike. A win against Nottingham Forest was equalled by victories over Leicester City and Gillingham Town – including goals in both games from the mid-season signing George Weah, drafted into the side as Sutton continued to flounder. That took us to the semis where Newcastle United awaited. Poyet – quickly becoming a hero of this FA Cup run – opened the scoring in the first-half but Rob Lee equalised after the interval. The Uruguayan confirmed his status as cup hero however, scoring minutes later to put Chelsea into an insurmountable lead.

Chelsea had made it into another Wembley final, three years after beating Middlesbrough in our last FA Cup final appearance. Di Matteo scored his 43-second opener that time, but he needed 73 minutes in 2000 to find the net. A dull final was briefly illuminated by the Italian, who pounced after Villa ‘keeper David James flapped at a Zola free-kick. Chelsea were FA Cup winners once again, and Vialli added another trophy to his CV.

1999/2000 was a season where we broke new boundaries for the club, making headway in new competitions and announcing our arrival on the major stage of European football. Although we perhaps did so at the expense of the Premiership and League Cup, and FA Cup win proved our growing stature in the domestic game too.