1. Round | 30/08/2008 | Olympiakos Piraeus | - | Asteras Tripolis | 3:1 | ||||
3. Round | 21/09/2008 | Olympiakos Piraeus | - | Panserraikos | 4:1 | ||||
12. Round | 30/11/2008 | Olympiakos Piraeus | - | Panionios GSS | 4:1 | ||||
13. Round | 07/12/2008 | Olympiakos Piraeus | - | Levadiakos | 1:0 | ||||
23. Round | 22/02/2009 | Ergotelis | - | Olympiakos Piraeus | 1:0 | ||||
25. Round | 08/03/2009 | PAOK Saloniki | - | Olympiakos Piraeus | 0:0 | ||||
27. Round | 22/03/2009 | Panionios GSS | - | Olympiakos Piraeus | 2:3 |