1999–2000 Chelsea F.C. season FA Cup FA Cup

| Date_ | Round | Opponent | Venue | Result_ | Attendance | Scorers |
|---|---|---|---|---|---|---|
| 11 December 1999 | R3 | Hull City | A | 6-1 | 10279 | Poyet (3), Sutton , Di Matteo , Wise |
| 19 January 2000 | R4 | Nottingham Forest | H | 2-0 | 30125 | Leboeuf , Wise |
| 30 January 2000 | R5 | Leicester City | H | 2-1 | 30141 | Poyet , Weah |
| 20 February 2000 | QF | Gillingham | H | 5-0 | 34205 | Flo , Terry , Weah , Zola ( pen. ), Morris |
| 9 April 2000 | SF | Newcastle United | N | 2-1 | 73876 | Poyet (2) |
| 20 May 2000 | F | Aston Villa | N | 1-0 | 78217 | Di Matteo |