1999–2000 Middlesbrough F.C. season League Cup League Cup

| Round | Date_ | Opponent | Venue | Result_ | Attendance |
|---|---|---|---|---|---|
| R2 1st Leg | 14 September 1999 | Chesterfield | A | 0–0 | 4941 |
| R2 2nd Leg | 21 September 1999 | Chesterfield | H | 2–1 (won 2-1 on agg) | 25602 |
| R3 | 13 October 1999 | Watford | H | 1–0 | 8846 |
| R4 | 30 November 1999 | Arsenal | H | 2–2 (won 3-1 on pens) | 23157 |
| R5 | 14 December 1999 | Tranmere Rovers | A | 1–2 | 10581 |