| Yellow | Clubs | VS Club | Date | Sections | |
|---|---|---|---|---|---|
| 5 | Arsenal | Leicester City | 09-01-2000 | Fourth Round | Match details |
| 5 | Leicester City | Arsenal | 09-01-2000 | Fourth Round | Match details |
| 4 | Leicester City | Chelsea | 30-01-2000 | Fifth Round | Match details |
| 4 | Chelsea | Leicester City | 30-01-2000 | Fifth Round | Match details |
| 3 | Chelsea | Aston Villa | 20-05-2000 | Final | Match details |
| 2 | Aston Villa | Chelsea | 20-05-2000 | Final | Match details |
| 2 | Blackburn Rovers | Liverpool | 10-01-2000 | Fourth Round | Match details |
| 1 | Chelsea | Newcastle United | 09-04-2000 | Semi Final | Match details |
| 1 | Gillingham | Chelsea | 20-02-2000 | Sixth Round | Match details |
| 1 | Chelsea | Gillingham | 20-02-2000 | Sixth Round | Match details |
