Major League Soccer 1999 |
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| Date | Round | Round | H/A | | | | Res. |
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| 20.03.1999 | Matchday 1 | Matchday 1 | A |  | Tampa Bay Mutin | W | 5:20:0 |
| 03.04.1999 | Matchday 2 | Matchday 2 | A |  | New York RB | W | 1:00:0 |
| 10.04.1999 | Matchday 2 | Matchday 2 | A |  | New Engl. | W | 3:2pso |
| 17.04.1999 | Matchday 2 | Matchday 2 | H |  | Earthquakes | L | 1:2pso |
| 24.04.1999 | Matchday 2 | Matchday 2 | H |  | New Engl. | L | 2:31:3 |
| 01.05.1999 | Matchday 3 | Matchday 3 | A |  | Chicago Fire | L | 2:30:1 |
| 08.05.1999 | Matchday 3 | Matchday 3 | H |  | New York RB | W | 2:11:0 |
| 15.05.1999 | Matchday 3 | Matchday 3 | A |  | Kansas City | W | 4:3pso |
| 22.05.1999 | Matchday 3 | Matchday 3 | A |  | Miami Fusion | W | 3:10:0 |
| 29.05.1999 | Matchday 3 | Matchday 3 | H |  | Chicago Fire | W | 3:11:1 |
| 05.06.1999 | Matchday 4 | Matchday 4 | H |  | Columbus Crew | W | 1:00:0 |
| 10.06.1999 | Matchday 4 | Matchday 4 | H |  | Miami Fusion | W | 3:12:0 |
| 13.06.1999 | Matchday 4 | Matchday 4 | A |  | Columbus Crew | W | 2:11:0 |
| 16.06.1999 | Matchday 4 | Matchday 4 | A |  | FC Dallas | L | 0:30:0 |
| 19.06.1999 | Matchday 4 | Matchday 4 | H |  | L.A. Galaxy | L | 1:20:1 |
| 26.06.1999 | Matchday 4 | Matchday 4 | H |  | Kansas City | W | 3:00:0 |
| 04.07.1999 | Matchday 5 | Matchday 5 | A |  | Earthquakes | L | 1:2pso |
| 07.07.1999 | Matchday 5 | Matchday 5 | A |  | Columbus Crew | W | 2:1pso |
| 10.07.1999 | Matchday 5 | Matchday 5 | H |  | Colorado Rapids | L | 1:20:0 |
| 25.07.1999 | Matchday 5 | Matchday 5 | A |  | New Engl. | W | 2:02:0 |
| 08.08.1999 | Matchday 6 | Matchday 6 | H |  | Tampa Bay Mutin | W | 3:2pso |
| 11.08.1999 | Matchday 6 | Matchday 6 | A |  | New York RB | W | 4:12:1 |
| 14.08.1999 | Matchday 6 | Matchday 6 | H |  | Columbus Crew | W | 2:11:0 |
| 21.08.1999 | Matchday 6 | Matchday 6 | A |  | Miami Fusion | W | 3:2pso |
| 25.08.1999 | Matchday 6 | Matchday 6 | H |  | Miami Fusion | W | 3:13:1 |
| 28.08.1999 | Matchday 6 | Matchday 6 | A |  | Colorado Rapids | W | 1:01:0 |
| 04.09.1999 | Matchday 7 | Matchday 7 | H |  | FC Dallas | W | 4:12:1 |
| 10.09.1999 | Matchday 7 | Matchday 7 | A |  | Tampa Bay Mutin | W | 2:12:0 |
| 18.09.1999 | Matchday 7 | Matchday 7 | H |  | New York RB | W | 2:1pso |
| 25.09.1999 | Matchday 7 | Matchday 7 | A |  | L.A. Galaxy | W | 2:01:0 |
| 06.10.1999 | Matchday 8 | Matchday 8 | H |  | Tampa Bay Mutin | L | 2:40:2 |
| 09.10.1999 | Matchday 8 | Matchday 8 | H |  | New Engl. | L | 1:2pso |
Major League Soccer 1999 Playoffs |
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| Date | Round | Round | H/A | | | | Res. |
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| 16.10.1999 | Quarter-finals, 0. Match | Quarter-Finals, 0. Match | H |  | Miami Fusion | W | 2:01:0 |
| 24.10.1999 | Quarter-finals, 0. Match | Quarter-Finals, 0. Match | A |  | Miami Fusion | W | 1:0pso |
| 31.10.1999 | Semi-finals, 0. Match | Semi-Final, 0. Match | H |  | Columbus Crew | W | 2:11:0 |
| 07.11.1999 | Semi-finals, 0. Match | Semi-Final, 0. Match | A |  | Columbus Crew | L | 1:51:2 |
| 13.11.1999 | Semi-finals, 0. Match | Semi-Final, 0. Match | H |  | Columbus Crew | W | 4:02:0 |
| 21.11.1999 | Final | Final | A |  | L.A. Galaxy | W | 2:02:0 |