1998–99 Chelsea F.C. season FA Cup FA Cup

| Date_ | Round | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|---|
| 2 January 1999 | R3 | Oldham Athletic | A | 2-0 | 12770 |
| 25 January 1999 | R4 | Oxford United | A | 1-1 | 9059 |
| 3 February 1999 | R4 (R) | Oxford United | H | 4-2 | 32106 |
| 13 February 1999 | R5 | Sheffield Wednesday | A | 1-0 | 29410 |
| 7 March 1999 | R6 | Manchester United | A | 0-0 | 54587 |
| 10 March 1999 | R6 (R) | Manchester United | H | 0-2 | 33075 |