European football's most prestigious prize continues to prove an elusive Holy Grail for London clubs, with last night's defeat for Chelsea taking the search full circle.

After all, they missed out more than half a century ago when invited to become the first English club to take part in the European Cup. But for the short-sighted objections of the Football League, they might have been realistic challengers to the first winners, Real Madrid.

When FIFA gave their blessing to the idea of a knockout tournament for Europe's league winners in May 1955, Chelsea, the English champions, were one of 18 clubs asked to take part. Others included Hibernian, AC Milan, Rapid Vienna, Partizan Belgrade, PSV, Sporting Lisbon and Real.

By the time the first European Champion Clubs' Cup kicked off in September that year, Chelsea had been advised to withdraw. Club chairman Joe Mears was keen to embrace the new tournament but he was also a member of the Football League's management committee and, in the end, bowed to their argument that additional fixtures would be difficult to fit in.

By the time Chelsea pulled out, the first-round draw had already been made. They were due to play Djurgarden of Sweden. Gwardia Warsaw, from Poland, replaced Chelsea and were beaten 4-1 on aggregate by the Swedes.

So, Manchester United, champions of the old First Division in 1955-56, became the first English side to take part the following season. They reached the semi-finals before losing 5-3 on aggregate to the great Madrid side that dominated the early years of the tournament.

The modern Chelsea have made three semi-final appearances in four seasons but Tottenham were the first London club to reach the last four in 1961-62.

Bill Nicholson's wonderful team had completed the League and FA Cup 'Double' the previous season but made a woeful start to their European campaign, losing 4-2 to Gornik in Poland and going a goal down in the home leg.

But they suddenly discovered a bit of form and ended up winning 8-1 at White Hart Lane. Spurs then beat Feyenoord and Dukla Prague before facing holders Benfica in the semi-finals.

Even the presence of new record signing Jimmy Greaves could not save them. Beaten 3-1 in Lisbon, Spurs won the home leg 2-1 and hit the woodwork three times but it wasn't enough.

Arsenal's 'Double' winners of 1971 were the next London club to challenge seriously but they were knocked out in the quarter-finals by the Ajax team of Cruyff, Neeskens and Krol. Having lost the first leg 2-1 in Amsterdam, they appeared to have a good chance at Highbury until George Graham headed into his own goal.

London fans had to wait more than 30 years for the next realistic stab at the European title. Although Arsenal again reached the last eight in 2001 - eventually losing on away goals to Spanish side Valencia - it was not until 2003-04 that the capital hosted a semi-final, as Chelsea emerged as a new force.

They progressed from a 5-0 aggregate win over Zilina in the third qualifying round to the semi-finals with wins against Sparta Prague, Lazio, Besiktas, Stuttgart and Arsenal.

Hernan Crespo's goal provided a life-line in a 3-1 first-leg defeat in Monaco but the Blues could only draw 2-2 at Stamford Bridge. So Monaco advanced to the final, where they lost 3-0 to Jose Mourinho's Porto.

The following season, under the leadership of new boss Mourinho, Chelsea beat Paris SG, Porto, CSKA Moscow, Barcelona and Bayern Munich before losing 1-0 on aggregate to Luis Garcia's 'ghost goal' against eventual winners Liverpool at Anfield in the semi-final.

In 2005-06, Arsenal swept past FC Thun, Ajax, Sparta Prague, Real Madrid, Juventus and Villarreal to reach the final. They faced Barcelona in Paris, a difficult job made even harder by the dismissal of goalkeeper Jens Lehmann for a foul on Samuel Eto'o.

Nonetheless, Sol Campbell headed the 10 men in front after 34 minutes, only for Eto'o to equalise and Brazilian full-back Juliano Belletti, now with Chelsea, to score the winner nine minutes from time.

Last season, as Arsenal stumbled in the first knockout round, Chelsea beat Werder Bremen, Levski Sofia, Barcelona, Porto and Valencia to reach the semi-final, only for Liverpool to prove unsurpassable at Anfield, winning via a penalty shoot-out.

And Liverpool proved a stumbling block again this season as they beat Arsenal 5-3 on aggregate in the quarterfinals.