Sunday 22 February
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 4h30 |   Portland Timbers vs Columbus Crew | 3 - 2 | Major League Soccer Phase : J1 | Providence Park |
Saturday 28 February
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 22h30 |  Colorado Rapids vs Portland Timbers | 2 - 0 | Major League Soccer Phase : J2 | Dick's Sporting Goods Park |
Sunday 8 March
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 4h30 |  Portland Timbers vs Vancouver Whitecaps | 1 - 4 | Major League Soccer Phase : J3 | Providence Park |
Sunday 15 March
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h30 |  Houston Dynamo vs Portland Timbers | 3 - 2 | Major League Soccer Phase : J4 | Stade Shell Energy |
Sunday 22 March
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 21h45 |  Portland Timbers vs Los Angeles Galaxy | 1 - 1 | Major League Soccer Phase : J5 | Providence Park |
Sunday 5 April
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Vancouver Whitecaps vs Portland Timbers | 3 - 2 | Major League Soccer Phase : J6 | BC Place |
Saturday 11 April
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 21h45 |  Portland Timbers vs Los Angeles FC | 2 - 1 | Major League Soccer Phase : J7 | Providence Park |
Sunday 19 April
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h30 |  Minnesota United FC vs Portland Timbers | 2 - 0 | Major League Soccer Phase : J8 | Allianz Field |
Sunday 26 April
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 2h30 |  San Diego vs Portland Timbers | 1 - 2 | Major League Soccer Phase : J10 | Stade Snapdragon |
Saturday 2 May
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 21h45 |  Real Salt Lake vs Portland Timbers | 2 - 0 | Major League Soccer Phase : J11 | America First Field |
Sunday 10 May
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs Sporting Kansas City | 6 - 0 | Major League Soccer Phase : J12 | Providence Park |
Thursday 14 May
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 0h30 |  CF Montreal vs Portland Timbers | 2 - 2 | Major League Soccer Phase : J13 | Stade Saputo |
Sunday 17 May
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 23h00 |  Inter Miami vs Portland Timbers | 2 - 0 | Major League Soccer Phase : J14 | Stade Nu |
Sunday 24 May
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 2h30 |  Portland Timbers vs San Jose Earthquakes | 1 - 3 | Major League Soccer Phase : J15 | Providence Park |
Friday 17 July
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Seattle Sounders vs Portland Timbers | 1 - 5 | Major League Soccer Phase : J16 | Lumen Field |
Thursday 23 July
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs FC Dallas | 2 - 2 | Major League Soccer Phase : J16 | Providence Park |
Sunday 26 July
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Portland Timbers vs Real Salt Lake | 2 - 1 | Major League Soccer Phase : J17 | Providence Park |
Sunday 2 August
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h45 | Portland Timbers vs Seattle Sounders | - | Major League Soccer Phase : J18 | Providence Park |
Sunday 16 August
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 23h00 |  Chicago Fire vs Portland Timbers | - | Major League Soccer Phase : J19 | Soldier Field |
Thursday 20 August
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Portland Timbers vs San Diego | - | Major League Soccer Phase : J20 | Providence Park |
Sunday 23 August
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Los Angeles FC vs Portland Timbers | - | Major League Soccer Phase : J21 | Stade BMO |
Sunday 30 August
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs Austin | - | Major League Soccer Phase : J22 | Providence Park |
Sunday 6 September
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Portland Timbers vs Minnesota United FC | - | Major League Soccer Phase : J23 | Providence Park |
Thursday 10 September
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs St. Louis City | - | Major League Soccer Phase : J24 | Providence Park |
Sunday 13 September
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h30 | FC Dallas vs Portland Timbers | - | Major League Soccer Phase : J25 | Stade Toyota |
Sunday 20 September
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs Atlanta United FC | - | Major League Soccer Phase : J26 | Providence Park |
Sunday 27 September
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | San Jose Earthquakes vs Portland Timbers | - | Major League Soccer Phase : J27 | PayPal Park |
Sunday 11 October
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h30 | Sporting Kansas City vs Portland Timbers | - | Major League Soccer Phase : J28 | Children's Mercy Park |
Thursday 15 October
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Los Angeles Galaxy vs Portland Timbers | - | Major League Soccer Phase : J29 | Dignity Health Sports Park |
Sunday 18 October
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 | Portland Timbers vs Colorado Rapids | - | Major League Soccer Phase : J30 | Providence Park |
Sunday 25 October
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h30 |  Portland Timbers vs Charlotte | - | Major League Soccer Phase : J31 | Providence Park |
Thursday 29 October
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h30 | St. Louis City vs Portland Timbers | - | Major League Soccer Phase : J32 | CITYPARK |
Monday 2 November
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 3h00 | Portland Timbers vs Houston Dynamo | - | Major League Soccer Phase : J33 | Providence Park |
Sunday 8 November
| Heure | Match | Score | Compétition | Stade |
|---|---|---|---|---|
| 1h00 | Austin vs Portland Timbers | - | Major League Soccer Phase : J34 | Stade Q2 |