29/05 - 20:00
W | 1990-02-06 | Middlesbrough |  | 2-1(a.e.t.) |  | Aston Villa | F | ||
W | 1990-01-30 | Aston Villa | | 1-2 | | Middlesbrough | F | ||
W | 1990-01-23 | Middlesbrough | | 1-0 |  | Newcastle | SF | ||
W | 1989-12-20 | Middlesbrough | | 4-1 |  | Sheffield Wed. | 3R | ||
W | 1989-11-29 | Middlesbrough | | 3-1 |  | Port Vale | 2R | ||
L | 1989-05-13 | Sheffield Wed. | | 1-0 | | Middlesbrough | D37 | ||
L | 1989-05-06 | Middlesbrough | | 0-1 |  | Arsenal | D35 | ||
D | 1989-04-29 | Aston Villa | | 1-1 | | Middlesbrough | D35 | ||
L | 1989-04-22 | Middlesbrough | | 3-4 |  | Nottingham Forest | D35 | ||
D | 1989-04-15 | QPR |  | 0-0 | | Middlesbrough | D34 | ||
W | 1989-04-11 | West Ham |  | 1-2 | | Middlesbrough | D33 | ||
D | 1989-04-08 | Middlesbrough | | 3-3 |  | Southampton | D31 | ||
L | 1989-04-01 | Charlton Athletic |  | 2-0 | | Middlesbrough | D31 | ||
D | 1989-03-27 | Middlesbrough | | 3-3 |  | Everton | D29 | ||
D | 1989-03-25 | Wimbledon |  | 1-1 | | Middlesbrough | D27 | ||
L | 1989-03-18 | Middlesbrough | | 0-1 |  | Derby County | D27 | ||
L | 1989-03-11 | Middlesbrough | | 0-4 |  | Liverpool | D25 | ||
D | 1989-02-26 | Middlesbrough | | 1-1 | | Newcastle | D26 | ||
L | 1989-02-21 | Millwall |  | 2-0 | | Middlesbrough | D25 | ||
L | 1989-02-18 | Luton Town |  | 1-0 | | Middlesbrough | D24 |
