
| Overall | Div 1 | |
| Wins | 479 | 181 |
| Draws | 212 | 88 |
| Losses | 475 | 178 |
| Pct. | 0.502 | 0.503 |
| FC Dallas (DAL) | S15 - S15 |
| Columbus Crew (CLB) | S15 - S15 |
| New England Revolution (NE) | S17 - S17 |
| Carolina Railhawks (CAR) | S17 - S17 |
| Atlanta Silverbacks (ATL) | S21 - S21 |
| John Holden (S3-13), Vacant (S4-29), Dave Dowson (S15-15), Phil McIntosh (S15-15), Steve Allan (S17-17), Steve Turner (S17-17), Jason Dowson (S17-17), David Blair (S18-19), Paul Cockayne (S20-23), Bryce Kalmbach (S21-21), Derek Purvis (S24-31), |
| M | DATE | SCORE | OPPONENT | COMPETITION | HEAD TO HEAD RESULTS | LAST MATCH | |||
| 1 | Sep 20 | San Jose Earthquakes | Allan Sellers Cup | Portland Timbers lead series 25-15-24 | POR 3-2 (Sea-35) | ||||
| 2 | Sep 23 | @ | Atlanta United | Allan Sellers Cup | Atlanta United lead series 23-11-20 | ATL 2-0 (Sea-37) | |||
| 3 | Sep 27 | Charleston Battery | Allan Sellers Cup | Portland Timbers lead series 24-9-15 | CHA 4-2 (Sea-37) | ||||
| 4 | Sep 30 | @ | Charleston Battery | Allan Sellers Cup | Portland Timbers lead series 24-9-15 | CHA 4-2 (Sea-37) | |||
| 5 | Oct 04 | Atlanta United | Allan Sellers Cup | Atlanta United lead series 23-11-20 | ATL 2-0 (Sea-37) | ||||
| 6 | Oct 07 | @ | San Jose Earthquakes | Allan Sellers Cup | Portland Timbers lead series 25-15-24 | POR 3-2 (Sea-35) | |||
| 7 | Oct 11 | @ | Los Angeles FC | Division 1 | Portland Timbers lead series 9-1-1 | POR 6-1 (Sea-37) | |||
| 8 | Oct 14 | @ | Houston Dynamo | Division 1 | Portland Timbers lead series 26-9-23 | POR 2-1 (Sea-36) | |||
| 9 | Oct 18 | Austin FC | Division 1 | Portland Timbers lead series 9-3-3 | POR 4-1 (Sea-37) | ||||
| 10 | Oct 21 | @ | Columbus Crew | Division 1 | Columbus Crew lead series 33-9-30 | POR 5-0 (Sea-36) | |||
| 11 | Oct 25 | @ | Atlanta United | Division 1 | Atlanta United lead series 23-11-20 | ATL 2-0 (Sea-37) | |||
| 13 | Nov 01 | Charleston Battery | Division 1 | Portland Timbers lead series 24-9-15 | CHA 4-2 (Sea-37) | ||||
| 15 | Nov 08 | @ | Carolina RailHawks | Division 1 | Carolina RailHawks lead series 42-9-24 | CAR 5-0 (Sea-37) | |||
| 17 | Nov 15 | (n) | Los Angeles FC | Division 1 | Portland Timbers lead series 9-1-1 | POR 6-1 (Sea-37) | |||
| 18 | Nov 18 | (n) | Houston Dynamo | Division 1 | Portland Timbers lead series 26-9-23 | POR 2-1 (Sea-36) | |||
| 19 | Nov 22 | (n) | Austin FC | Division 1 | Portland Timbers lead series 9-3-3 | POR 4-1 (Sea-37) | |||
| 20 | Nov 25 | (n) | Columbus Crew | Division 1 | Columbus Crew lead series 33-9-30 | POR 5-0 (Sea-36) | |||
| 21 | Nov 29 | (n) | Atlanta United | Division 1 | Atlanta United lead series 23-11-20 | ATL 2-0 (Sea-37) | |||
| 22 | Dec 02 | (n) | Charleston Battery | Division 1 | Portland Timbers lead series 24-9-15 | CHA 4-2 (Sea-37) | |||
| 23 | Dec 06 | (n) | Carolina RailHawks | Division 1 | Carolina RailHawks lead series 42-9-24 | CAR 5-0 (Sea-37) | |||
| 25 | Dec 13 | Los Angeles FC | Division 1 | Portland Timbers lead series 9-1-1 | POR 6-1 (Sea-37) | ||||
| 27 | Dec 20 | Houston Dynamo | Division 1 | Portland Timbers lead series 26-9-23 | POR 2-1 (Sea-36) | ||||
| 29 | Jan 03 | @ | Austin FC | Division 1 | Portland Timbers lead series 9-3-3 | POR 4-1 (Sea-37) | |||
| 31 | Jan 10 | Columbus Crew | Division 1 | Columbus Crew lead series 33-9-30 | POR 5-0 (Sea-36) | ||||
| 33 | Jan 17 | Atlanta United | Division 1 | Atlanta United lead series 23-11-20 | ATL 2-0 (Sea-37) | ||||
| 35 | Jan 24 | @ | Charleston Battery | Division 1 | Portland Timbers lead series 24-9-15 | CHA 4-2 (Sea-37) | |||
| 37 | Jan 31 | Carolina RailHawks | Division 1 | Carolina RailHawks lead series 42-9-24 | CAR 5-0 (Sea-37) | ||||