25/04 - 20:00
| 1990/03/25 | Chelsea |  | 1-0 |  | Middlesbrough |
| 1st Leg | 2nd Leg | |||||||
|---|---|---|---|---|---|---|---|---|
 | (2-4) | | 1-2 | 1-2 a.e.t. |
| 1990/01/17 | Aston Villa | | 2-0 |  | Leeds United | ||||
| 1990/01/23 | Middlesbrough | | 1-0 |  | Newcastle |
| 1990/01/23 | Ipswich Town |  | 2-3 | | Chelsea | ||||
| 1990/02/13 | Crystal Palace |  | 1-0 |  | Swindon Town |
| 1989/12/19 | Crystal Palace | | 2-0 |  | Charlton Athletic | ||||
| 1989/12/21 | Ipswich Town | | 3-1 |  | Wimbledon | ||||
| 1989/12/22 | Chelsea | | 4-3 |  | West Ham | ||||
| 1990/01/24 | Swindon Town | | 4-1 |  | Norwich City |
| 1989/11/14 | Charlton Athletic | | 2-1 |  | Leicester City | ||||
| 1989/11/21 | Ipswich Town | | 4-1 |  | Watford | ||||
| 1989/11/27 | Crystal Palace | | 4-1 |  | Luton Town | ||||
| 1989/11/28 | Bournemouth |  | 2-3 a.e.t. | | Chelsea | ||||
| 1989/11/29 | West Ham | | 5-2 a.e.t. |  | Plymouth Argyle | ||||
| Norwich City | | 5-0 |  | Brighton & Hove Albion | |||||
| 1989/12/05 | Portsmouth |  | 0-1 | | Wimbledon | ||||
| 1989/12/13 | Swindon Town | | 2-1 |  | Millwall |
| 1989/11/08 | Oxford United |  | 2-3 a.e.t. | | Luton Town | ||||
| 1989/11/29 | Coventry City |  | 1-3 a.e.t. | | Wimbledon |
| 2 |
|
David Gregory Ipswich Town | 4 G |
| 3 |
|
Kerry Dixon Chelsea | 3 G |
| 3 |
|
Alan Dikens Chelsea | 3 G |
| 3 |
|
Kevin Wilson Chelsea | 3 G |
