Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 26.08.1995 |  | Matchday 3 | Middlesbrough - Chelsea | MID - CHE | 2:0 | 28.286 |
| 12.09.1995 | | Matchday 2 | Middlesbrough - Southampton | MID - SOU | 0:0 | 29.181 |
| 16.09.1995 | | Matchday 6 | Middlesbrough - Coventry | MID - COV | 2:1 | 27.882 |
| 20.09.1995 |  | 2. Round First leg | Middlesbrough - Rotherham Utd | MID - ROT | 2:1 | 13.280 |
| 30.09.1995 | | Matchday 8 | Middlesbrough - Blackburn | MID - BLA | 2:0 | 29.462 |
| 21.10.1995 | | Matchday 10 | Middlesbrough - QPR | MID - QPR | 1:0 | 29.293 |
| 04.11.1995 | | Matchday 12 | Middlesbrough - Leeds Utd | MID - LEE | 1:1 | 29.467 |
| 08.11.1995 | | 3. Round Repeat | Middlesbrough - Cr. Palace | MID - CPA | 2:0 | 16.150 |
| 14.11.1995 |  | Group 6 | England - Austria | ENG - AUT | 2:1 | 13.496 |
| 21.11.1995 | | Matchday 14 | Middlesbrough - Tottenham | MID - TOT | 0:1 | 29.487 |
| 25.11.1995 | | Matchday 15 | Middlesbrough - Liverpool | MID - LIV | 2:1 | 29.390 |
| 29.11.1995 | | Round of 16 | Middlesbrough - Birmingham | MID - BIR | 0:0 | 28.031 |
| 09.12.1995 | | Matchday 17 | Middlesbrough - Man City | MID - MCI | 4:1 | 29.469 |
| 23.12.1995 | | Matchday 19 | Middlesbrough - West Ham | MID - WHU | 4:2 | 28.540 |