| USA USL Championship | 2016/05/24 23:00 | Penn FC v Toronto FC II | L | 2-1 |
| USA USL Championship | 2016/06/21 23:00 | Louisville City FC v Toronto FC II | L | 4-1 |
| USA USL Championship | 2016/06/18 23:00 | FC Cincinnati v Toronto FC II | L | 2-1 |
| USA USL Championship | 2016/06/15 15:30 | Toronto FC II v FC Montreal | D | 1-1 |
| USA USL Championship | 2016/06/11 23:30 | Toronto FC II v RNY FC | W | 2-1 |
| USA USL Championship | 2016/05/29 23:30 | Toronto FC II v Wilmington Hammerheads | L | 1-3 |
| USA USL Championship | 2016/05/24 23:00 | Penn FC v Toronto FC II | L | 2-1 |
| USA USL Championship | 2016/05/21 23:00 | Pittsburgh Riverhounds v Toronto FC II | L | 2-1 |
| USA USL Championship | 2016/05/14 23:30 | Charleston Battery v Toronto FC II | L | 2-0 |
| USA USL Championship | 2016/06/21 23:00 | Penn FC v FC Montreal | L | 2-3 |
| USA USL Championship | 2016/06/18 23:30 | Charleston Battery v Penn FC | L | 1-0 |
| USA US Open Cup | 2016/06/15 23:00 | Philadelphia Union v Penn FC | L | 3-2 |
| USA USL Championship | 2016/06/09 23:00 | New York Red Bulls II v Penn FC | L | 1-0 |
| USA USL Championship | 2016/06/03 23:00 | Wilmington Hammerheads v Penn FC | L | 3-2 |
| USA US Open Cup | 2016/06/01 23:30 | Chattanooga FC v Penn FC | W | 1-2 |
| USA USL Championship | 2016/05/28 23:00 | FC Cincinnati v Penn FC | L | 2-0 |
| USA USL Championship | 2016/05/24 23:00 | Penn FC v Toronto FC II | W | 2-1 |