1997–98 Chelsea F.C. season League Cup League Cup

| Date_ | Round | Opponent | Venue | Result_ | Attendance | Scorers |
|---|---|---|---|---|---|---|
| 15 October 1997 | 3 | Blackburn Rovers | H | 1-1 | 18671 | Di Matteo |
| After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties | After extra time, Chelsea won on 4-1 on penalties |
| 19 November 1997 | 4 | Southampton | H | 2-1 | 20968 | Morris , Flo |
| 7 January 1998 | QF | Ipswich Town | A | 2-2 | 22088 | Le Saux , Flo |