Now defunct, the Cup Winners’ Cup was contested annually by teams that had won their domestic cup competition. It ran for 39 seasons and Chelsea played in it for the first time in the 1970-1971 season, winning it in their debut campaign. It wasn’t an easy journey to the final either, having had to defeat fellow English side Manchester City in the semi-final and Spanish giants Real Madrid in the final. Originally known as the European Cup Winners’ Cup, it was re-named as the UEFA Cup Winners’ Cup in 1994, with Chelsea winning it under its new name four years later.
Chelsea qualified for the competition for the first time by winning the FA Cup in 1970, which was also the competition that they won to make it into the Cup Winners’ Cup in order to win it again in 1998. A League Cup win that season meant that they qualified for the Cup Winners’ Cup via that route for the 1998-1999 iteration of the tournament, which was the last time that it was played before being discontinued. Chelsea made it to the semi-final stage that year, losing to Mallorca thanks to a 1-0 defeat in the second-leg after the two sides drew the first-leg 1-1.
| Season | Chelsea Result | Winner | Runner Up |
|---|---|---|---|
| 1998-1999 | Semi-Finals | Lazio | Mallorca |
| 1997-1998 | Winners | Chelsea | VfB Stuttgart |
| 1994-1995 | Semi-Finals | Real Zaragoza | Arsenal |
| 1971-1972 | Second Round | Rangers | Dynamo Moscow |
| 1970-1971 | Winners | Chelsea | Real Madrid |
Chelsea European Cup Winners’ Cup Wins
1997-1998: Chelsea 1-0 VfB Stuttgart
Firstly under Ruud Gullit and latterly under Gianluca Vialli, Chelsea had an excellent 1997/98 season winning two trophies, one of them being the Cup Winners’ Cup. In beating Slovan Bratislava (4-0), Tromso (9-4) and Real Betis (5-2) over two legs, Chelsea’s passage to the semi-finals proved to be rather easy.
A nervy semi was to follow, but a 3-2 win over Vicenza put the Blues into the final to play Stuttgart in Stockholm and no mistake was to be made, Vialli’s team coming out 1-0 winners there with a goal from club hero Gianfranco Zola.
1970-1971: Chelsea 1-1 (2-1 replay) Real Madrid
Chelsea’s first ever European success came in the 1970/71 season when after a dream run, the club landed in the final of the Cup Winners’ Cup and played Real Madrid in Athens.
A win looked inevitable at 1-0 and with time nearly up in the final, however a very late goal from Zoco took the match to a replay two days later. In the second game, John Dempsey and Peter Osgood came up with what was necessary to land a 2-1 win for the Blues.