Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 10.01.1990 |  | 3. Round Repeat | Oldham Athletic - Birmingham | OLD - BIR | 1:0 | 9.982 |
| 27.01.1990 | | 4. Round | Oldham Athletic - Brighton & Hove | OLD - BHA | 2:1 | 11.034 |
| 31.01.1990 |  | Quarter-finals Repeat | Oldham Athletic - Southampton | OLD - SOU | 2:0 | 18.862 |
| 14.02.1990 | | Semi-finals First leg | Oldham Athletic - West Ham | OLD - WHU | 6:0 | 19.263 |
| 17.02.1990 | | Round of 16 | Oldham Athletic - Everton | OLD - EVE | 2:2 | 19.320 |
| 10.03.1990 | | Round of 16 | Oldham Athletic - Everton | OLD - EVE | 2:1 | 19.346 |
| 14.03.1990 | | Quarter-finals | Oldham Athletic - Aston Villa | OLD - AVL | 3:0 | 19.490 |
| 10.10.1990 | | 2. Round 2nd leg | Oldham Athletic - Notts County | OLD - NOT | 5:2 | 10.757 |