
| Overall | Div 1 | |
| Wins | 482 | 182 |
| Draws | 215 | 90 |
| Losses | 480 | 180 |
| Pct. | 0.501 | 0.502 |
| Columbus Crew (CLB) | S15 - S15 |
| FC Dallas (DAL) | S15 - S15 |
| Carolina Railhawks (CAR) | S17 - S17 |
| New England Revolution (NE) | 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 | W | 2 - 1 | San Jose Earthquakes | Allan Sellers Cup | Portland Timbers lead series 26-16-24 | |||
| 2 | Sep 23 | L | 0 - 1 | @ | Atlanta United | Allan Sellers Cup | Atlanta United lead series 26-11-20 | ||
| 3 | Sep 27 | W | 3 - 1 | Charleston Battery | Allan Sellers Cup | Portland Timbers lead series 25-9-16 | |||
| 4 | Sep 30 | L | 1 - 2 | @ | Charleston Battery | Allan Sellers Cup | Portland Timbers lead series 25-9-16 | ||
| 5 | Oct 04 | L | 0 - 2 | Atlanta United | Allan Sellers Cup | Atlanta United lead series 26-11-20 | |||
| 6 | Oct 07 | D | 3 - 3 | @ | San Jose Earthquakes | Allan Sellers Cup | Portland Timbers lead series 26-16-24 | ||
| 7 | Oct 11 | L | 1 - 4 | @ | Los Angeles FC | Division 1 | Portland Timbers lead series 9-1-2 | ||
| 8 | Oct 14 | D | 4 - 4 | @ | Houston Dynamo | Division 1 | Portland Timbers lead series 26-10-23 | ||
| 9 | Oct 18 | W | 4 - 1 | Austin FC | Division 1 | Portland Timbers lead series 10-3-3 | |||
| 10 | Oct 21 | D | 2 - 2 | @ | Columbus Crew | Division 1 | Columbus Crew lead series 33-10-30 | ||
| 11 | Oct 25 | L | 0 - 1 | @ | Atlanta United | Division 1 | Atlanta United lead series 26-11-20 | ||
| 13 | Nov 01 | Charleston Battery | Division 1 | Portland Timbers lead series 25-9-16 | CHA 2-1 (Sea-38) | ||||
| 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 9-1-2 | LAF 4-1 (Sea-38) | |||
| 18 | Nov 18 | (n) | Houston Dynamo | Division 1 | Portland Timbers lead series 26-10-23 | Draw 4-4 (Sea-38) | |||
| 19 | Nov 22 | (n) | Austin FC | Division 1 | Portland Timbers lead series 10-3-3 | POR 4-1 (Sea-38) | |||
| 20 | Nov 25 | (n) | Columbus Crew | Division 1 | Columbus Crew lead series 33-10-30 | Draw 2-2 (Sea-38) | |||
| 21 | Nov 29 | (n) | Atlanta United | Division 1 | Atlanta United lead series 26-11-20 | ATL 1-0 (Sea-38) | |||
| 22 | Dec 02 | (n) | Charleston Battery | Division 1 | Portland Timbers lead series 25-9-16 | CHA 2-1 (Sea-38) | |||
| 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 9-1-2 | LAF 4-1 (Sea-38) | ||||
| 27 | Dec 20 | Houston Dynamo | Division 1 | Portland Timbers lead series 26-10-23 | Draw 4-4 (Sea-38) | ||||
| 29 | Jan 03 | @ | Austin FC | Division 1 | Portland Timbers lead series 10-3-3 | POR 4-1 (Sea-38) | |||
| 31 | Jan 10 | Columbus Crew | Division 1 | Columbus Crew lead series 33-10-30 | Draw 2-2 (Sea-38) | ||||
| 33 | Jan 17 | Atlanta United | Division 1 | Atlanta United lead series 26-11-20 | ATL 1-0 (Sea-38) | ||||
| 35 | Jan 24 | @ | Charleston Battery | Division 1 | Portland Timbers lead series 25-9-16 | CHA 2-1 (Sea-38) | |||
| 37 | Jan 31 | Carolina RailHawks | Division 1 | Carolina RailHawks lead series 42-9-24 | CAR 5-0 (Sea-37) | ||||