| Date | Round | Round | H/A | Res. | |||
|---|---|---|---|---|---|---|---|
| 30.08.2008 | Matchday 2 | Matchday 2 | A | ![]() | Español | D | 1:1 |
| 13.09.2008 | Matchday 4 | Matchday 4 | H | ![]() | River Plate | L | 0:2 |
| 20.09.2008 | Matchday 5 | Matchday 5 | A | ![]() | Peñarol | L | 0:3 |
| 27.09.2008 | Matchday 6 | Matchday 6 | H | ![]() | Nacional | L | 2:3 |
| 04.10.2008 | Matchday 7 | Matchday 7 | A | ![]() | CA Cerro | D | 1:1 |
| 18.10.2008 | Matchday 8 | Matchday 8 | H | ![]() | Liverpool FC | D | 1:1 |
| 25.10.2008 | Matchday 3 | Matchday 3 | H | ![]() | Racing | D | 0:0 |
| 01.11.2008 | Matchday 9 | Matchday 9 | A | ![]() | Defensor | L | 1:3 |
| 09.11.2008 | Matchday 10 | Matchday 10 | A | ![]() | Bella Vista | L | 2:5 |
| 15.11.2008 | Matchday 11 | Matchday 11 | H | ![]() | Española | W | 2:0 |
| 06.12.2008 | Matchday 12 | Matchday 12 | A | ![]() | Juventud | D | 1:1 |
| 14.12.2008 | Matchday 13 | Matchday 13 | H | ![]() | Tacuarembó | L | 0:2 |
| 18.12.2008 | Matchday 14 | Matchday 14 | A | ![]() | Wanderers | L | 0:1 |
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