| TRI1 |
2008 |
8 |
North East Stars |
2 - 2 |
St Ann's Rangers |
|
1 |
| TRI1 |
2008 |
8 |
Ma Pau |
2 - 1 |
United Petrotrin |
|
1 |
| TRI1 |
2008 |
8 |
Caledonia AIA |
1 - 2 |
Joe Public F.C. |
|
1 |
| TRI1 |
2008 |
8 |
San Juan Jabloteh |
1 - 0 |
W Connection |
|
1 |
| TRI1 |
2008 |
8 |
Defence Force |
1 - 1 |
Tobago United |
|
1 |
| USOC |
2008 |
2 |
Atlanta Silverbacks |
0 - 1 |
Miami FC |
Tropical Park Stadium |
1 |
| USOC |
2008 |
2 |
Cleveland City Stars |
2 - 0 |
Minnesota Thunder |
National Sports Center Stadium |
1 |
| USOC |
2008 |
2 |
Hollywood United |
0 - 6 |
Seattle Sounders |
Starfire Sports Complex |
1 |
| USOC |
2008 |
2 |
Crystal Palace Baltimore |
2 - 2 |
Harrisburg City Islanders |
Skyline Sports Complex |
1 |
| USOC |
2008 |
2 |
Richmond Kickers |
2 - 1 |
Western Mass Pioneers |
Lusitano Stadium |
1 |
| USOC |
2008 |
2 |
Carolina RailHawks |
1 - 0 |
Real Maryland Monarchs |
WakeMed Soccer Park |
1 |
| USOC |
2008 |
2 |
Charleston Battery |
2 - 1 |
Charlotte Eagles |
Blackbaud Stadium |
1 |