Round 27
|
| Thursday, 2 October 2008 |
| FC Dallas - San Jose |
| Saturday, 4 October 2008 |
| D.C. United - Chivas USA |
| Colorado Rapids - Houston Dynamo |
| New York - Toronto FC |
| Columbus Crew - L.A. Galaxy |
| N.E. Revolution - Real Salt Lake |
| Sunday, 5 October 2008 |
| K.C. Wizards - Chicago Fire |
Round 28
|
| Thursday, 9 October 2008 |
| Real Salt Lake - New York |
| Saturday, 11 October 2008 |
| FC Dallas - Toronto FC |
| K.C. Wizards - N.E. Revolution |
| San Jose - Chivas USA |
| Sunday, 12 October 2008 |
| Chicago Fire - Columbus Crew |
| Houston Dynamo - D.C. United |
| L.A. Galaxy - Colorado Rapids |
Round 29
|
| Thursday, 16 October 2008 |
| D.C. United - N.E. Revolution |
| Saturday, 18 October 2008 |
| Toronto FC - Chicago Fire |
| Houston Dynamo - L.A. Galaxy |
| New York - Columbus Crew |
| K.C. Wizards - San Jose |
| Real Salt Lake - FC Dallas |
| Sunday, 19 October 2008 |
| Chivas USA - Colorado Rapids |
Round 30
|
| Thursday, 23 October 2008 |
| Chicago Fire - New York |
| Saturday, 25 October 2008 |
| Colorado Rapids - Real Salt Lake |
| N.E. Revolution - K.C. Wizards |
| Chivas USA - Houston Dynamo |
| San Jose - Toronto FC |
| Sunday, 26 October 2008 |
| Columbus Crew - D.C. United |
| L.A. Galaxy - FC Dallas |
Major League 2008