FC Iskra-Stal 0-2 Sheriff Tiraspol
| 23.11.2008 | Sheriff Tiraspol | 0-0 | FC Iskra-Stal | |
| 05.11.2008 | FC Iskra-Stal | 0-2 | Sheriff Tiraspol | |
FC Tiraspol 3-3 Olimpia Balti
| 23.11.2008 | Olimpia Balti | 2-2 | FC Tiraspol | |
| 05.11.2008 | FC Tiraspol | 1-1 | Olimpia Balti | |
Nistru Otaci 0-3 Zimbru Chisinau
| 24.11.2008 | Zimbru Chisinau | 3-0 | Nistru Otaci | |
| 05.11.2008 | Nistru Otaci | 0-0 | Zimbru Chisinau | |
Tiligul-Tiras 1-3 Dacia Chisinau
| 22.11.2008 | Dacia Chisinau | 2-0 | Tiligul-Tiras | |
| 05.11.2008 | Tiligul-Tiras | 1-1 | Dacia Chisinau | |