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| H (Match allé) | New England Revolution | - | Chicago Fire | 0:0 (0:0) | ||
| R (match retour) | Chicago Fire | - | New England Revolution | 3:0 (1:0) | ||
| H (Match allé): 31.10.2008 00:30 | R (match retour): 07.11.2008 02:30 | vainqueur: Chicago Fire | ||||
| H (Match allé) | New York RB | - | Houston Dynamo | 1:1 (0:0) | ||
| R (match retour) | Houston Dynamo | - | New York RB | 0:3 (0:2) | ||
| H (Match allé): 01.11.2008 21:00 | R (match retour): 09.11.2008 21:00 | vainqueur: New York RB | ||||
| H (Match allé) | Real Salt Lake | - | CD Chivas | 1:0 (0:0) | ||
| R (match retour) | CD Chivas | - | Real Salt Lake | 2:2 (1:1) | ||
| H (Match allé): 01.11.2008 23:00 | R (match retour): 09.11.2008 04:30 | vainqueur: Real Salt Lake | ||||
| H (Match allé) | Kansas City Wizards | - | Columbus Crew | 1:1 (0:0) | ||
| R (match retour) | Columbus Crew | - | Kansas City Wizards | 2:0 (1:0) | ||
| H (Match allé): 02.11.2008 01:00 | R (match retour): 09.11.2008 01:30 | vainqueur: Columbus Crew | ||||
