| 10.10.1999 | | Columbus Crew | | Chicago Fire | | 2:3 (1:0), pen. 1:2 |
| Columbus |
| 10.10.1999 | | Tampa Bay Mutiny | | Dallas Burn | | 1:2 (0:1) |
| Tampa |
| 09.10.1999 | | D.C. United | | New England Revolution | | 1:2, pen. 2:3 |
| Washington |
| 09.10.1999 | | Kansas City Wizards | | Los Angeles Galaxy | | 0:1 (0:1) |
| Kansas City |
| 09.10.1999 | | Miami Fusion | | Colorado Rapids | | 2:0 (0:0) |
| Fort Lauderdale |
| 06.10.1999 | | Colorado Rapids | | Chicago Fire | | 0:1 (0:1) |
| Denver |
| 06.10.1999 | | D.C. United | | Tampa Bay Mutiny | | 2:4 (0:2) |
| Washington |
| 06.10.1999 | | San Jos? Clash | | Kansas City Wizards | | 1:0 (0:0) |
| San Jos? |
| 03.10.1999 | | Dallas Burn | | Los Angeles Galaxy | | 4:3 (1:2) |
| Dallas |
| 03.10.1999 | | Miami Fusion | | Columbus Crew | | 4:1 (3:0) |
| Fort Lauderdale |
| 02.10.1999 | | New England Revolution | | MetroStars | | 2:1 (1:0) |
| Foxborough |
| 01.10.1999 | | Colorado Rapids | | San Jos? Clash | | 1:0 (0:0), pen. 3:0 |
| Denver |
| 29.09.1999 | | Los Angeles Galaxy | | Colorado Rapids | | 4:0 (2:0) |
| Pasadena |
| 26.09.1999 | | Columbus Crew | | Miami Fusion | | 2:1 (0:1) |
| Columbus |
| 26.09.1999 | | San Jos? Clash | | Chicago Fire | | 2:0 (0:0) |
| San Jos? |
| 25.09.1999 | | Kansas City Wizards | | Colorado Rapids | | 0:1 (0:0), pen. 2:3 |
| Kansas City |
| 25.09.1999 | | Los Angeles Galaxy | | D.C. United | | 0:2 (0:1) |
| Pasadena |
| 25.09.1999 | | Tampa Bay Mutiny | | MetroStars | | 1:2 (1:2) |
| Tampa |
| 24.09.1999 | | New England Revolution | | Dallas Burn | | 0:1 (0:0) |
| Foxborough |
| 23.09.1999 | | Chicago Fire | | Columbus Crew | | 1:2 (1:2) |
| Chicago |
| 22.09.1999 | | MetroStars | | San Jos? Clash | | 1:2 (1:1) |
| East Rutherford |
| 19.09.1999 | | San Jos? Clash | | Miami Fusion | | 6:1 (2:0) |
| San Jos? |
| 18.09.1999 | | Colorado Rapids | | Los Angeles Galaxy | | 1:0 (1:0) |
| Denver |
| 18.09.1999 | | D.C. United | | MetroStars | | 2:1 (1:0), pen. 2:1 |
| Washington |
| 18.09.1999 | | Kansas City Wizards | | Dallas Burn | | 1:2 (0:0), pen. 0:3 |
| Kansas City |
| 18.09.1999 | | New England Revolution | | Columbus Crew | | 0:1 (0:0), pen. 1:4 |
| Foxborough |
| 17.09.1999 | | Chicago Fire | | Tampa Bay Mutiny | | 2:1 (1:1), pen. 4:3 |
| Chicago |
| 12.09.1999 | | Columbus Crew | | MetroStars | | 1:2 (1:1) |
| Columbus |
| 11.09.1999 | | Dallas Burn | | San Jos? Clash | | 1:0 (0:0) |
| Dallas |
| 11.09.1999 | | Los Angeles Galaxy | | Chicago Fire | | 1:0 (0:0) |
| Pasadena |
| 11.09.1999 | | Miami Fusion | | New England Revolution | | 2:1 (1:1), pen. 3:2 |
| Fort Lauderdale |
| 10.09.1999 | | Colorado Rapids | | Kansas City Wizards | | 1:0 (0:0), pen. 3:2 |
| Denver |
| 10.09.1999 | | Tampa Bay Mutiny | | D.C. United | | 1:2 (0:2) |
| Tampa |
| 07.09.1999 | | New England Revolution | | Kansas City Wizards | | 3:2 (0:1) |
| Foxborough |
| 05.09.1999 | | MetroStars | | Chicago Fire | | 1:2 (0:0) |
| East Rutherford |
| 04.09.1999 | | Columbus Crew | | Colorado Rapids | | 2:1 (1:1) |
| Columbus |
| 04.09.1999 | | D.C. United | | Dallas Burn | | 4:1 (2:1) |
| Washington |
| 04.09.1999 | | Miami Fusion | | Los Angeles Galaxy | | 1:2 |
| Fort Lauderdale |
| 04.09.1999 | | New England Revolution | | Tampa Bay Mutiny | | 1:5 (1:3) |
| Foxborough |
| 04.09.1999 | | San Jos? Clash | | Kansas City Wizards | | 2:0 (1:0) |
| San Jos? |
| 01.09.1999 | | Los Angeles Galaxy | | San Jos? Clash | | 3:1 (1:0) |
| Pasadena |
| 29.08.1999 | | Kansas City Wizards | | Miami Fusion | | 2:0 (1:0) |
| Kansas City |
| 28.08.1999 | | Chicago Fire | | New England Revolution | | 2:1 (2:0) |
| Chicago |
| 28.08.1999 | | Colorado Rapids | | D.C. United | | 0:1 (0:1) |
| Denver |
| 28.08.1999 | | Dallas Burn | | Los Angeles Galaxy | | 1:0 (0:0) |
| Dallas |
| 28.08.1999 | | San Jos? Clash | | MetroStars | | 2:1 (0:1), pen. 4:3 |
| San Jos? |
| 27.08.1999 | | Tampa Bay Mutiny | | Columbus Crew | | 2:1 (1:0) |
| Tampa |
| 25.08.1999 | | Chicago Fire | | Kansas City Wizards | | 2:0 (0:0) |
| Chicago |
| 25.08.1999 | | D.C. United | | Miami Fusion | | 3:1 (3:1) |
| Washington |
| 25.08.1999 | | MetroStars | | New England Revolution | | 1:2 (1:0), pen. 1:3 |
| East Rutherford |
| 22.08.1999 | | Columbus Crew | | Tampa Bay Mutiny | | 1:2 (1:0), pen. 0:3 |
| Columbus |
| 22.08.1999 | | Dallas Burn | | Chicago Fire | | 4:3 (2:0), pen. 4:3 |
| Dallas |
| 21.08.1999 | | Los Angeles Galaxy | | MetroStars | | 4:1 (2:0) |
| Pasadena |
| 21.08.1999 | | Miami Fusion | | D.C. United | | 2:3 (0:0), pen. 0:2 |
| Fort Lauderdale |
| 21.08.1999 | | San Jos? Clash | | New England Revolution | | 2:1 (1:1) |
| San Jos? |
| 18.08.1999 | | Colorado Rapids | | Dallas Burn | | 0:3 (0:2) |
| Denver |
| 18.08.1999 | | MetroStars | | Columbus Crew | | 2:4 (1:1) |
| East Rutherford |
| 18.08.1999 | | New England Revolution | | Tampa Bay Mutiny | | 0:1 (0:1) |
| Foxborough |
| 14.08.1999 | | Chicago Fire | | Miami Fusion | | 1:2 (1:0), pen. 0:3 |
| Chicago |
| 14.08.1999 | | D.C. United | | Columbus Crew | | 2:1 (1:0) |
| Washington |
| 14.08.1999 | | Los Angeles Galaxy | | Dallas Burn | | 2:0 |
| Pasadena |
| 14.08.1999 | | MetroStars | | Kansas City Wizards | | 1:2 (1:1) |
| East Rutherford |
| 13.08.1999 | | Tampa Bay Mutiny | | Colorado Rapids | | 0:1 (0:0) |
| Tampa |
| 12.08.1999 | | New England Revolution | | San Jos? Clash | | 1:2 (1:0) |
| Foxborough |
| 11.08.1999 | | MetroStars | | D.C. United | | 1:4 (1:2) |
| East Rutherford |
| 08.08.1999 | | Chicago Fire | | Colorado Rapids | | 5:0 (1:0) |
| Chicago |
| 08.08.1999 | | Columbus Crew | | Kansas City Wizards | | 2:1 (1:0) |
| Columbus |
| 08.08.1999 | | D.C. United | | Tampa Bay Mutiny | | 3:2 (1:1), pen. 3:2 |
| Washington |
| 07.08.1999 | | Miami Fusion | | MetroStars | | 2:0 (0:0) |
| Fort Lauderdale |
| 07.08.1999 | | San Jos? Clash | | Los Angeles Galaxy | | 1:4 (0:1) |
| San Jos? |
| 06.08.1999 | | Colorado Rapids | | New England Revolution | | 1:0 (0:0), pen. 3:2 |
| Denver |
| 05.08.1999 | | Kansas City Wizards | | Chicago Fire | | 1:2 (0:2) |
| Kansas City |
| 04.08.1999 | | Dallas Burn | | MetroStars | | 2:0 (0:0) |
| Dallas |
| 01.08.1999 | | Columbus Crew | | Miami Fusion | | 4:0 (2:0) |
| Columbus |
| 31.07.1999 | | Chicago Fire | | Los Angeles Galaxy | | 0:1 (0:1) |
| Chicago |
| 31.07.1999 | | Dallas Burn | | Colorado Rapids | | 0:2 (0:1) |
| Dallas |
| 31.07.1999 | | Kansas City Wizards | | San Jos? Clash | | 3:2 (1:1), pen. 2:1 |
| Kansas City |
| 31.07.1999 | | Tampa Bay Mutiny | | New England Revolution | | 4:1 (2:0) |
| Tampa |
| 29.07.1999 | | Miami Fusion | | Tampa Bay Mutiny | | 3:2 (0:2), pen. 3:2 |
| Fort Lauderdale |
| 28.07.1999 | | Colorado Rapids | | Los Angeles Galaxy | | 1:0 (1:0) |
| Denver |
| 25.07.1999 | | Colorado Rapids | | Tampa Bay Mutiny | | 2:3 (1:1), pen. 2:3 |
| Denver |
| 25.07.1999 | | Los Angeles Galaxy | | Kansas City Wizards | | 2:1 (2:1) |
| Pasadena |
| 25.07.1999 | | New England Revolution | | D.C. United | | 0:2 (0:2) |
| Foxborough |
| 24.07.1999 | | Columbus Crew | | Dallas Burn | | 4:1 (2:0) |
| Columbus |
| 24.07.1999 | | MetroStars | | Miami Fusion | | 0:1 (0:0) |
| East Rutherford |
| 23.07.1999 | | Chicago Fire | | San Jos? Clash | | 2:3 (1:0), pen. 0:2 |
| Chicago |
| 22.07.1999 | | Kansas City Wizards | | Tampa Bay Mutiny | | 4:3 (1:1) |
| Kansas City |
| 11.07.1999 | | New England Revolution | | Los Angeles Galaxy | | 2:5 (1:1) |
| Foxborough |
| 10.07.1999 | | Chicago Fire | | MetroStars | | 2:0 (1:0) |
| Chicago |
| 10.07.1999 | | D.C. United | | Colorado Rapids | | 1:2 (0:0) |
| Washington |
| 10.07.1999 | | Dallas Burn | | Kansas City Wizards | | 5:0 (1:0) |
| Dallas |
| 10.07.1999 | | Miami Fusion | | Columbus Crew | | 2:0 (1:0) |
| Fort Lauderdale |
| 08.07.1999 | | Tampa Bay Mutiny | | San Jos? Clash | | 2:1 (1:1) |
| Tampa |
| 07.07.1999 | | Columbus Crew | | D.C. United | | 1:2 (0:1), pen. 0:2 |
| Columbus |
| 07.07.1999 | | Kansas City Wizards | | Colorado Rapids | | 1:2 (1:2) |
| Kansas City |
| 04.07.1999 | | Colorado Rapids | | Columbus Crew | | 0:3 (0:1) |
| Denver |
| 04.07.1999 | | Dallas Burn | | Chicago Fire | | 1:2 |
| Dallas |
| 04.07.1999 | | Los Angeles Galaxy | | Miami Fusion | | 1:2 (1:1) |
| Pasadena |
| 04.07.1999 | | New England Revolution | | MetroStars | | 3:2 (2:1) |
| Foxborough |
| 04.07.1999 | | San Jos? Clash | | D.C. United | | 2:1 (1:1), pen. 3:2 |
| Palo Alto |
| 03.07.1999 | | Tampa Bay Mutiny | | Kansas City Wizards | | 1:2 (1:1), pen. 2:3 |
| Tampa |
| 02.07.1999 | | Chicago Fire | | Dallas Burn | | 2:1 (0:1), pen. 4:3 |
| Chicago |
| 30.06.1999 | | Columbus Crew | | San Jos? Clash | | 4:3 (1:1), pen. 2:1 |
| Columbus |
| 30.06.1999 | | MetroStars | | Tampa Bay Mutiny | | 2:1 (0:0), pen. 3:2 |
| East Rutherford |
| 27.06.1999 | | Tampa Bay Mutiny | | Los Angeles Galaxy | | 2:4 (0:0) |
| Tampa |
| 26.06.1999 | | Colorado Rapids | | Chicago Fire | | 2:0 (0:0) |
| Denver |
| 26.06.1999 | | Columbus Crew | | MetroStars | | 2:1 (1:0) |
| Columbus |
| 26.06.1999 | | D.C. United | | Kansas City Wizards | | 3:0 (0:0) |
| Washington |
| 26.06.1999 | | Dallas Burn | | New England Revolution | | 2:0 (1:0) |
| Dallas |
| 26.06.1999 | | Miami Fusion | | San Jos? Clash | | 1:2 (1:2) |
| Fort Lauderdale |
| 20.06.1999 | | Kansas City Wizards | | MetroStars | | 6:0 (4:0) |
| Kansas City |
| 19.06.1999 | | Chicago Fire | | San Jos? Clash | | 2:0 (1:0) |
| Chicago |
| 19.06.1999 | | Colorado Rapids | | Dallas Burn | | 2:1 (1:1) |
| Denver |
| 19.06.1999 | | D.C. United | | Los Angeles Galaxy | | 1:2 (0:1) |
| Washington |
| 19.06.1999 | | Tampa Bay Mutiny | | New England Revolution | | 2:3 (1:1) |
| Tampa |
| 16.06.1999 | | Columbus Crew | | New England Revolution | | 2:1 (1:1), pen. 2:1 |
| Columbus |
| 16.06.1999 | | Dallas Burn | | D.C. United | | 3:0 (0:0) |
| Dallas |
| 13.06.1999 | | Columbus Crew | | D.C. United | | 1:2 (0:1) |
| Columbus |
| 13.06.1999 | | New England Revolution | | Miami Fusion | | 4:3 (1:1), pen. 3:1 |
| Foxborough |
| 12.06.1999 | | Kansas City Wizards | | Dallas Burn | | 1:0 (0:0) |
| Kansas City |
| 12.06.1999 | | Los Angeles Galaxy | | Chicago Fire | | 2:1 (2:0) |
| Pasadena |
| 12.06.1999 | | MetroStars | | Colorado Rapids | | 0:1 (0:0) |
| East Rutherford |
| 12.06.1999 | | San Jos? Clash | | Tampa Bay Mutiny | | 2:1 (1:1), pen. 1:0 |
| San Jos? |
| 10.06.1999 | | D.C. United | | Miami Fusion | | 3:1 (2:0) |
| Washington |
| 06.06.1999 | | Los Angeles Galaxy | | Kansas City Wizards | | 1:0 (0:0) |
| Pasadena |
| 05.06.1999 | | D.C. United | | Columbus Crew | | 1:0 (0:0) |
| Washington |
| 05.06.1999 | | MetroStars | | Dallas Burn | | 2:5 (0:2) |
| East Rutherford |
| 05.06.1999 | | New England Revolution | | Chicago Fire | | 2:0 (1:0) |
| Foxborough |
| 05.06.1999 | | Tampa Bay Mutiny | | Miami Fusion | | 1:0 (1:0) |
| Tampa |
| 03.06.1999 | | San Jos? Clash | | Colorado Rapids | | 4:3 (1:2) |
| San Jos? |
| 29.05.1999 | | Columbus Crew | | Los Angeles Galaxy | | 2:1 (0:0), pen. 3:0 |
| Columbus |
| 29.05.1999 | | D.C. United | | Chicago Fire | | 3:1 (1:1) |
| Washington |
| 29.05.1999 | | MetroStars | | New England Revolution | | 3:4 (1:2), pen. 0:1 |
| East Rutherford |
| 29.05.1999 | | Miami Fusion | | Tampa Bay Mutiny | | 2:1 (1:0) |
| Fort Lauderdale |
| 27.05.1999 | | Colorado Rapids | | San Jos? Clash | | 4:2 (1:1) |
| Denver |
| 26.05.1999 | | Dallas Burn | | Miami Fusion | | 2:1 (1:0) |
| Dallas |
| 23.05.1999 | | Los Angeles Galaxy | | New England Revolution | | 1:0 (1:0) |
| Pasadena |
| 22.05.1999 | | Chicago Fire | | Kansas City Wizards | | 3:1 (2:0) |
| Chicago |
| 22.05.1999 | | Colorado Rapids | | MetroStars | | 2:0 (1:0) |
| Denver |
| 22.05.1999 | | Columbus Crew | | Tampa Bay Mutiny | | 0:1 (0:0), pen. 1:3 |
| Columbus |
| 22.05.1999 | | Miami Fusion | | D.C. United | | 1:3 (0:0) |
| Fort Lauderdale |
| 22.05.1999 | | San Jos? Clash | | Dallas Burn | | 2:1 (1:0), pen. 3:1 |
| San Jos? |
| 16.05.1999 | | Chicago Fire | | Colorado Rapids | | 0:1 (0:1) |
| Chicago |
| 15.05.1999 | | Columbus Crew | | New England Revolution | | 2:0 (1:0) |
| Columbus |
| 15.05.1999 | | Dallas Burn | | San Jos? Clash | | 2:1 (1:1) |
| Dallas |
| 15.05.1999 | | Kansas City Wizards | | D.C. United | | 3:4 (3:1), pen. 0:3 |
| Kansas City |
| 15.05.1999 | | Los Angeles Galaxy | | Tampa Bay Mutiny | | 0:1 (0:0), pen. 2:4 |
| Pasadena |
| 15.05.1999 | | MetroStars | | Miami Fusion | | 3:2 (2:0) |
| East Rutherford |
| 09.05.1999 | | San Jos? Clash | | Columbus Crew | | 1:2 (1:1) |
| San Jos? |
| 08.05.1999 | | D.C. United | | MetroStars | | 2:1 (1:0) |
| Washington |
| 08.05.1999 | | Dallas Burn | | Colorado Rapids | | 1:2 (0:0), pen. 1:2 |
| Dallas |
| 08.05.1999 | | Kansas City Wizards | | Los Angeles Galaxy | | 2:1 (2:1) |
| Kansas City |
| 08.05.1999 | | New England Revolution | | Miami Fusion | | 1:0 (0:0), pen. 3:2 |
| Foxborough |
| 08.05.1999 | | Tampa Bay Mutiny | | Chicago Fire | | 2:1 (0:1), pen. 1:0 |
| Tampa |
| 01.05.1999 | | Chicago Fire | | D.C. United | | 3:2 (1:0) |
| Chicago |
| 01.05.1999 | | MetroStars | | Los Angeles Galaxy | | 0:1 (0:0), pen. 2:3 |
| East Rutherford |
| 01.05.1999 | | New England Revolution | | Colorado Rapids | | 1:2 (1:1) |
| Foxborough |
| 01.05.1999 | | Tampa Bay Mutiny | | Miami Fusion | | 2:1 (2:0) |
| Tampa |
| 30.04.1999 | | San Jos? Clash | | Dallas Burn | | 2:1 (1:1), pen. 3:2 |
| San Jos? |
| 28.04.1999 | | Kansas City Wizards | | Columbus Crew | | 0:1 (0:0) |
| Kansas City |
| 25.04.1999 | | MetroStars | | Tampa Bay Mutiny | | 0:1 (0:1) |
| East Rutherford |
| 24.04.1999 | | D.C. United | | New England Revolution | | 2:3 (1:3) |
| Washington |
| 24.04.1999 | | Dallas Burn | | Columbus Crew | | 2:0 (2:0) |
| Dallas |
| 24.04.1999 | | Los Angeles Galaxy | | San Jos? Clash | | 1:0 (0:0) |
| Pasadena |
| 24.04.1999 | | Miami Fusion | | Kansas City Wizards | | 1:0 (1:0) |
| Fort Lauderdale |
| 18.04.1999 | | Dallas Burn | | Tampa Bay Mutiny | | 2:1 (1:0) |
| Dallas |
| 17.04.1999 | | Chicago Fire | | Los Angeles Galaxy | | 1:0 (1:0) |
| Chicago |
| 17.04.1999 | | Colorado Rapids | | Kansas City Wizards | | 2:1 (0:1), pen. 3:2 |
| Denver |
| 17.04.1999 | | D.C. United | | San Jos? Clash | | 1:2 (1:1), pen. 2:4 |
| Washington |
| 17.04.1999 | | New England Revolution | | Columbus Crew | | 0:1 (0:0), pen. 3:4 |
| Foxborough |
| 15.04.1999 | | Miami Fusion | | Dallas Burn | | 2:1 (0:0), pen. 3:0 |
| Fort Lauderdale |
| 11.04.1999 | | Tampa Bay Mutiny | | MetroStars | | 1:2 (0:1), pen. 1:3 |
| Tampa |
| 10.04.1999 | | Chicago Fire | | Dallas Burn | | 0:1 (0:0), pen. 1:3 |
| Chicago |
| 10.04.1999 | | Colorado Rapids | | Miami Fusion | | 4:1 (0:0) |
| Denver |
| 10.04.1999 | | Kansas City Wizards | | San Jos? Clash | | 1:2 (0:1), pen. 0:2 |
| Kansas City |
| 10.04.1999 | | New England Revolution | | D.C. United | | 2:3 (0:1), pen. 3:4 |
| Foxborough |
| 08.04.1999 | | Los Angeles Galaxy | | Columbus Crew | | 1:2 (0:0), pen. 2:3 |
| Pasadena |
| 03.04.1999 | | Kansas City Wizards | | New England Revolution | | 0:1 (0:1) |
| Kansas City |
| 03.04.1999 | | MetroStars | | D.C. United | | 0:1 (0:0) |
| East Rutherford |
| 03.04.1999 | | Miami Fusion | | Chicago Fire | | 1:4 (0:1) |
| Fort Lauderdale |
| 03.04.1999 | | San Jos? Clash | | Los Angeles Galaxy | | 2:1 (1:0), pen. 4:2 |
| San Jos? |
| 03.04.1999 | | Tampa Bay Mutiny | | Columbus Crew | | 2:3 (1:2) |
| Tampa |
| 28.03.1999 | | Los Angeles Galaxy | | Dallas Burn | | 1:0 (0:0), pen. 3:2 |
| Pasadena |
| 28.03.1999 | | MetroStars | | Columbus Crew | | 1:0 (0:0) |
| East Rutherford |
| 28.03.1999 | | Miami Fusion | | New England Revolution | | 2:1 (0:1), pen. 4:3 |
| Fort Lauderdale |
| 27.03.1999 | | Kansas City Wizards | | Chicago Fire | | 0:3 (0:1) |
| Kansas City |
| 27.03.1999 | | San Jos? Clash | | Colorado Rapids | | 3:2 (0:1), pen. 4:3 |
| San Jos? |
| 20.03.1999 | | Dallas Burn | | Kansas City Wizards | | 4:0 (0:0) |
| Dallas |
| 20.03.1999 | | Los Angeles Galaxy | | Colorado Rapids | | 2:1 (1:1), pen. 3:1 |
| Pasadena |
| 20.03.1999 | | Miami Fusion | | MetroStars | | 2:3 (0:1), pen. 1:2 |
| Fort Lauderdale |
| 20.03.1999 | | San Jos? Clash | | Chicago Fire | | 1:3 (1:0) |
| San Jos? |
| 20.03.1999 | | Tampa Bay Mutiny | | D.C. United | | 2:5 (0:0) |
| Tampa |