Head to Head
| USA USL League Two | 2019/05/18 02:00 | TSS FC Rovers v Portland Timbers U23 | L | 5-0 |
| USA USL PDL | 2018/07/07 01:30 | Portland Timbers U23 v TSS FC Rovers | L | 0-2 |
| USA USL PDL | 2018/05/19 02:00 | TSS FC Rovers v Portland Timbers U23 | L | 3-1 |
| USA USL PDL | 2017/06/17 02:00 | TSS FC Rovers v Portland Timbers U23 | D | 2-2 |
| USA USL PDL | 2017/06/03 02:00 | TSS FC Rovers v Portland Timbers U23 | D | 1-1 |
| USA USL PDL | 2017/05/17 02:00 | Portland Timbers U23 v TSS FC Rovers | W | 2-0 |
Home History
| USA USL League Two | 2019/06/16 21:00 | Victoria Highlanders v Portland Timbers U23 | L | 6-0 |
| USA USL League Two | 2019/06/15 02:30 | Seattle Sounders FC U23 v Portland Timbers U23 | D | 0-0 |
| USA USL League Two | 2019/06/09 02:00 | Lane United FC v Portland Timbers U23 | L | 3-0 |
| USA USL League Two | 2019/06/02 21:00 | Portland Timbers U23 v Calgary Foothills FC | D | 1-1 |
| USA USL League Two | 2019/06/01 02:00 | Portland Timbers U23 v Calgary Foothills FC | W | 2-1 |
| USA USL League Two | 2019/05/26 21:00 | Portland Timbers U23 v Lane United FC | L | 1-3 |
| USA USL League Two | 2019/05/25 02:00 | Portland Timbers U23 v Seattle Sounders FC U23 | L | 0-4 |
| USA USL League Two | 2019/05/19 21:00 | Victoria Highlanders v Portland Timbers U23 | L | 2-0 |
Away History
| USA USL League Two | 2019/06/22 02:00 | Lane United FC v TSS FC Rovers | L | 5-2 |
| USA USL League Two | 2019/06/16 21:00 | TSS FC Rovers v Seattle Sounders FC U23 | L | 0-2 |
| USA USL League Two | 2019/06/15 02:00 | TSS FC Rovers v Lane United FC | D | 1-1 |
| USA USL League Two | 2019/06/08 02:00 | TSS FC Rovers v Victoria Highlanders | L | 0-1 |
| USA USL League Two | 2019/05/26 20:00 | Calgary Foothills FC v TSS FC Rovers | D | 0-0 |
| USA USL League Two | 2019/05/25 01:00 | Calgary Foothills FC v TSS FC Rovers | L | 3-2 |
| USA USL League Two | 2019/05/19 21:00 | TSS FC Rovers v Calgary Foothills FC | L | 1-2 |
| USA USL League Two | 2019/05/18 02:00 | TSS FC Rovers v Portland Timbers U23 | W | 5-0 |