Round 24
|
| Wednesday, 3 September 2008 |
| Montreal Impact - Rochester Raging Rhinos |
| Puerto Rico Islanders - Vancouver Whitecaps |
Round 25
|
| Thursday, 4 September 2008 |
| Portland Timbers - Miami FC Blues |
| Friday, 5 September 2008 |
| Montreal Impact - Minnesota Thunder |
| Saturday, 6 September 2008 |
| Rochester Raging Rhinos - Portland Timbers |
| Seattle Sounders - Miami FC Blues |
| Carolina RailHawks - Charleston Battery |
| Sunday, 7 September 2008 |
| Vancouver Whitecaps - Minnesota Thunder |
Round 26
|
| Wednesday, 10 September 2008 |
| Seattle Sounders - Montreal Impact |
| Thursday, 11 September 2008 |
| Portland Timbers - Charleston Battery |
| Friday, 12 September 2008 |
| Rochester Raging Rhinos - Puerto Rico Islanders |
| Saturday, 13 September 2008 |
| Vancouver Whitecaps - Montreal Impact |
| Minnesota Thunder - Charleston Battery |
| Seattle Sounders - Atlanta Silverbacks |
Round 27
|
| Sunday, 14 September 2008 |
| Carolina RailHawks - Rochester Raging Rhinos |
| Wednesday, 17 September 2008 |
| Montreal Impact - Puerto Rico Islanders |
Round 29
|
| Friday, 19 September 2008 |
| Charleston Battery - Carolina RailHawks |
Round 30
|
| Puerto Rico Islanders - Atlanta Silverbacks |
| Saturday, 20 September 2008 |
| Minnesota Thunder - Montreal Impact |
| Seattle Sounders - Vancouver Whitecaps |
| Carolina RailHawks - Portland Timbers |
| Sunday, 21 September 2008 |
| Miami FC Blues - Atlanta Silverbacks |
USL-1 2008