| 1. Round | 06/09/1988 | VfB Stuttgart | - | Tatabanya Banyasz SC | 2:0 | ||||
| 1. Round | 11/10/1988 | Tatabanya Banyasz SC | - | VfB Stuttgart | 2:1 | ||||
| 2. Round | 25/10/1988 | Dinamo Zagreb | - | VfB Stuttgart | 1:3 | ||||
| 2. Round | 08/11/1988 | VfB Stuttgart | - | Dinamo Zagreb | 1:1 | ||||
| Round of 16 | 22/11/1988 | FC Groningen | - | VfB Stuttgart | 1:3 | ||||
| Round of 16 | 06/12/1988 | VfB Stuttgart | - | FC Groningen | 2:0 | ||||
| Quarter-finals | 27/02/1989 | VfB Stuttgart | - | Real Sociedad | 1:0 | ||||
| Quarter-finals | 14/03/1989 | Real Sociedad | - | VfB Stuttgart | 2:4 pso | ||||
| Semi-finals | 04/04/1989 | VfB Stuttgart | - | Dynamo Dresden | 1:0 | ||||
| Semi-finals | 18/04/1989 | Dynamo Dresden | - | VfB Stuttgart | 1:1 | ||||
| Final | 02/05/1989 | SSC Napoli | - | VfB Stuttgart | 2:1 | ||||
| Final | 16/05/1989 | VfB Stuttgart | - | SSC Napoli | 3:3 |
Iceland