| 3. Jornada | 17.05.2008 | Toronto FC | - | Columbus Crew | 0:0 | ||||
| 3. Jornada | 31.05.2008 | Toronto FC | - | Los Angeles Galaxy | 2:0 |  |
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| 4. Jornada | 09.06.2008 | Houston Dynamo | - | Toronto FC | 3:1 | ||||
| 4. Jornada | 29.06.2008 | New England Revolution | - | Toronto FC | 2:1 | ||||
| 5. Jornada | 13.07.2008 | Chicago Fire | - | Toronto FC | 2:1 | ||||
| 5. Jornada | 29.07.2008 | Real Salt Lake | - | Toronto FC | 2:1 | ||||
| 6. Jornada | 03.08.2008 | Toronto FC | - | FC Dallas | 0:2 | ||||
| 6. Jornada | 09.08.2008 | Colorado Rapids | - | Toronto FC | 0:1 | ||||
| 6. Jornada | 17.08.2008 | New York RB | - | Toronto FC | 2:0 | ||||
| 6. Jornada | 24.08.2008 | Toronto FC | - | New England Revolution | 1:1 | ||||
| 6. Jornada | 31.08.2008 | CD Chivas | - | Toronto FC | 2:1 | ||||
| 7. Jornada | 13.09.2008 | Toronto FC | - | Columbus Crew | 1:1 | ||||
| 7. Jornada | 21.09.2008 | Kansas City Wizards | - | Toronto FC | 2:0 | ||||
| 8. Jornada | 12.10.2008 | FC Dallas | - | Toronto FC | 2:2 |
Trinidad y Tobago