Chelsea have played Real Madrid 3 times in competitive football, winning 2, drawing 1 and losing 0, first meeting on 19 May 1971 and most recently on 28 Aug 1998. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 19 May 1971 | 1970–71 | UEFA Cup | H | Real Madrid | 1–1 | Peter Osgood | 45,000 |
| 21 May 1971 | 1970–71 | UEFA Cup | H | Real Madrid | 2–1 | John Dempsey, Peter Osgood | 24,000 |
| 28 Aug 1998 | 1998–99 | UEFA Cup | H | Real Madrid | 1–0 | Gustavo Poyet | 10,000 |