Chelsea’s first taste with the Champions League came in 1999-2000. It faced Latvian side Skonto in the third qualifying round. It got through this 3-0 on aggregate and was going to taste Champions League group action for the first time. Despite being in a group with Hertha Berlin, Galatasaray and AC Milan, Chelsea took to the Champions League like a duck to water and finished top of the group while Milan actually finished last. In the second group stage, Chelsea was paired with Lazio, Feyenoord and Marseille. It finished second in the group to advance to the quarter-finals.
You would have excused Chelsea for thinking that the Champions League was pretty simple. On its first attempt it had made it as far as the last eight and in the first leg of the quarter-final had beaten Barcelona 3-1 at home. It was in store for a shock in the return leg. Barcelona also won 3-1 to send it through to extra time and there Barcelona scored twice to wrap up the tie. Anders Frisk was in charge of this match and the significance of the Swede was to come later.
Chelsea returned to the competiton four years later. Again it topped it group which contained Sparta Prague, Besiktas and Lazio. It was drawn to play VFB Stuttgart in the Round of 16. It scored a 1-0 win in Stuttgart and followed that with a 0-0 draw.
The quarter finals saw an all-English tie in Arsenal taking on Chelsea. Despite Arsenal’s significant more experience in Europe, Chelsea were too good for them. A 1-1 draw at Stamford Bridge was followed by a 2-1 win at Highbury. Goal to Frank Lampard and Wayne Bridge proved the difference.
Chelsea was the only English side in the semi-finals and had to play Monaco. The first leg was in Monaco was 1-1 until the French managed two late goals. Chelsea got back into the tie with two goals, but Hugo Ibarra scored deep into first-half injury time to swing the tie Monaco’s way. When Fernando Morientes scored in the second half, the tie was over.
In 2004-05, Chelsea was in a group with Porto, CSKA Moscow and Paris Saint-Germain. The game against Porto was a spicy affair as Jose Mourinho had left Porto to manage Chelsea. Yet again Chelsea topped its group. In the round of 16 it was drawn to face Barcelona. A 2-1 loss in Barcelona was followed by a 4-2 at home. Three goals in the first 17 minutes tilted the tie in Chelsea’s favor. Didier Drogba was sent off by Anders Frisk and the Chelsea players and fans were very unhappy with this. Frisk received death threats and would retire from refereeing as a result of them.
In the quarter finals, Chelsea was up against another European giant in Bayern Munich. Chelsea won the opening leg in London 4-2 and then would have won the match in Munich 2-1 until two late goals to Bayern gave them the win. The tie was still Chelsea’s as it went through 6-5 on aggregate.
The semi final pitted Chelsea against Liverpool. After a scoreless first match at Stamford Bridge, Liverpool scored via a 4th minute Luis Garcia goal. This goal was highly controversial and sent Liverpool through to the final.
Liverpool won the final and was allowed to defend its title the following year, but wouldn’t have country protection rights in the opening rounds. This is how Chelsea found itself in a group with Liverpool, Real Betis and Anderlecht. Liverpool topped the group but Chelsea advanced as the second-best team. In the Round of 16, Chelsea was drawn with old for Barcelona. The opening leg in London saw Barcelona win 2-1 and it drew the second leg 1-1 to go through 3-2.
Unsurprisingly, the following year Chelsea found itself in a group with Barcelona. The other two sides were Werder Bremen and Levski Sofia. Chelsea topped the group. It got past first Porto and then Valencia in the knock out stages before finding itself yet again up against Liverpool. Both sides won 1-0 at home to send the tie to penalties. Liverpool didn’t miss a single penalty so the misses by Arjen Robben and Geremi proved fatal.
In 2007-08, Chelsea progressed past its group and then defeated Olympiacos and Fenerbahce in the knockout rounds. Once again, it faced Liverpool with a place in the final on the line.
The first game was at Anfield and a late John Arne Riise own goal gave Chelsea an equalizer and the away goal it so desperately craved. In the return leg, it was also 1-1 to send the tie to extra time. Goals to Frank Lampard and Didier Drogba gave Chelsea a cushion and not even a late Ryan Babel goal could prevent Chelsea from playing in the final.
As many finals are, the match was a very tense affair. The game opened up somewhat with a 26th minute goal to Ronaldo. Chelsea looked for an equalizer and Frank Lampard scored it just before half-time. This gave Chelsea a lot of confidence and it came out in the second half looking more assured. It was tight with Drogba hitting the post and Giggs missing a chance near the end of 90 minutes.
Heading to extra time, it got even crazier. Lampard hit the crossbar and Giggs was again denied – this time by a John Terry header off the line. Towards the end of the match tempers frayed and Drogba was sent off. This would prove vital as he wasn’t around to take a penalty in the shootout.
Of the first nine takers, only Ronaldo missed meaning a John Terry goal which give Chelsea the win. He slipped on the wet ground to hand United a life line. It took it when Van der Saar saved from Nicolas Anelka. So close but yet so horribly far.
In 2008-09, Chelsea got past Juventus before meeting Liverpool again. It won the first tie at Anfield 3-1 and then the return leg 4-4 in one of the most entertaining Champions League matches ever played. The semi final was against Barcelona and after a scoreless 0-0 draw, a late goal to Andrés Iniesta won the match for them. Like Anders Frisk before him, Norwegian referee Tom Hennig Ovrebo found himself in the firing line.
Give the competitiveness of Chelsea and their innate ability to play in Europe, it would seem only a matter of time before they win it all.