From TheChels.info - The Chelsea Football Club Wiki
The 1999-00 UEFA Champions League campaign was Chelsea's first in Europe's premier club competition, and their ninth European campaign overall. Though this was Chelsea's first appearance in the European Cup or Champions League, as English champions after the 1954-55 season the club was invited to enter the inaugural European Champions' Cup, but were forced to withdraw after pressure from the Football League.
Chelsea qualified by virtue of finishing third in the 1998-99 Premier League, but the position meant they had joined in the third qualifying round. After safely negotiating two legs against Skonto Riga, they were drawn in Group H of the competition proper along with AC Milan, Hertha Berlin and Galatasaray. With three wins, one loss, and two draws, including a memorable 1-1 draw at the San Siro, Chelsea topped the group to reach the second group stage.
Drawn against Feyenoord, Lazio and Marseille in Group D, Chelsea were on course to top the group before a 2-1 home defeat against Lazio (the club's first home defeat in European competition) allowed the Roman side to leapfrog the Blues, who qualified nonetheless in second place.
A 3-1 home win against Barcelona in the quarter-final first leg gave the Londoners the advantage, but the Catalan side matched Chelsea's score in the return leg, forcing the match into extra time. Barcelona then took control and scored twice in the additional period to end Chelsea's impressive debut season in the UEFA Champions League.
Qualifying round
| Season
| Day
| D
| M
| Year
| Round
| Opposition
| Venue
| Result
| Score
| Additional Information
|
| 1999-00 | Wed | 11 | Aug | 1999 | 3rd Qualifying Round 1st Leg | Skonto Riga | Home | Won | 3-0 |
|
| 1999-00 | Wed | 25 | Aug | 1999 | 3rd Qualifying Round 2nd Leg | Skonto Riga | Away | Drew | 0-0 | (3-0 aggregate)
|
1st Group Stage
Matches
Table
2nd Group Stage
Matches
Table
Knock-out rounds
| Season
| Day
| D
| M
| Year
| Round
| Opposition
| Venue
| Result
| Score
| Additional Information
|
| 1999-00 | Wed | 5 | Apr | 2000 | Quarter Final 1st Leg | Barcelona | Home | Won | 3-1 |
|
| 1999-00 | Tue | 18 | Apr | 2000 | Quarter Final 2nd Leg | Barcelona | Away | Lost | 1-5* | *aet (4-6 aggregate)
|
