1998–99 Chelsea F.C. season UEFA Cup Winners' Cup UEFA Cup Winners' Cup

| Date_ | Round | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|---|
| 17 September 1998 | R1 | Helsingborg | H | 1-0 | 17714 |
| 1 October 1998 | R1 | Helsingborg | A | 0-0 | 12348 |
| 22 October 1998 | R2 | Copenhagen | H | 1-1 | 21207 |
| 5 November 1998 | R2 | Copenhagen | A | 1-0 | 24188 |
| 4 March 1999 | QF | Vålerenga | H | 3-0 | 34177 |
| 18 March 1999 | QF | Vålerenga | A | 3-2 | 17936 |
| 8 April 1999 | SF | Mallorca | H | 1-1 | 35524 |
| 22 April 1999 | SF | Mallorca | A | 0-1 | 18848 |