series
| Oct. 18, 2008 | MLS | 2008 | Chicago Fire | 2 - 3 | Toronto FC | 1 | |
| July 12, 2008 | MLS | 2008 | Chicago Fire | 2 - 1 | Toronto FC | 1 |
scoreboard
| MLS | 2008 | Colorado Rapids | 1 - 1 | San Jose Earthquakes | 1 | |
| MLS | 2008 | Columbus Crew | 0 - 2 | Real Salt Lake | 1 |
| Oct. 18, 2008 | MLS | 2008 | Chicago Fire | 2 - 3 | Toronto FC | 1 | |
| July 12, 2008 | MLS | 2008 | Chicago Fire | 2 - 1 | Toronto FC | 1 |
| MLS | 2008 | Colorado Rapids | 1 - 1 | San Jose Earthquakes | 1 | |
| MLS | 2008 | Columbus Crew | 0 - 2 | Real Salt Lake | 1 |