Head to Head
| USA USL League One | 2019/10/05 23:00 | Richmond Kickers v Orlando City II | W | 2-0 |
| USA USL League One | 2019/07/20 23:00 | Richmond Kickers v Orlando City II | W | 1-0 |
| USA USL League One | 2019/05/22 23:30 | Orlando City II v Richmond Kickers | L | 3-2 |
| USA USL Championship | 2017/10/01 21:00 | Richmond Kickers v Orlando City II | L | 0-1 |
| USA USL Championship | 2017/09/07 20:30 | Orlando City II v Richmond Kickers | W | 0-2 |
| USA USL Championship | 2017/08/12 23:00 | Richmond Kickers v Orlando City II | L | 0-1 |
| USA USL Championship | 2016/08/27 23:00 | Richmond Kickers v Orlando City II | W | 1-0 |
| USA USL Championship | 2016/08/21 23:30 | Orlando City II v Richmond Kickers | D | 1-1 |
Home History
| USA USL League One | 2019/10/05 23:00 | Richmond Kickers v Orlando City II | W | 2-0 |
| USA USL League One | 2019/10/02 23:00 | Richmond Kickers v Toronto FC II | L | 1-2 |
| USA USL League One | 2019/09/28 23:00 | Chattanooga Red Wolves v Richmond Kickers | L | 2-1 |
| USA USL League One | 2019/09/22 02:30 | FC Tucson v Richmond Kickers | D | 0-0 |
| USA USL League One | 2019/09/14 23:00 | Richmond Kickers v Forward Madison FC | L | 0-1 |
| USA USL League One | 2019/09/11 00:00 | North Texas SC v Richmond Kickers | L | 4-0 |
| USA USL League One | 2019/09/07 23:00 | Richmond Kickers v Greenville Triumph SC | W | 1-0 |
| USA USL League One | 2019/09/01 00:00 | South Georgia Tormenta FC v Richmond Kickers | W | 1-4 |
Away History
| USA USL League One | 2019/10/05 23:00 | Richmond Kickers v Orlando City II | L | 2-0 |
| USA USL League One | 2019/09/27 23:00 | Greenville Triumph SC v Orlando City II | W | 0-1 |
| USA USL League One | 2019/09/21 23:00 | Chattanooga Red Wolves v Orlando City II | L | 2-1 |
| USA USL League One | 2019/09/13 20:00 | Toronto FC II v Orlando City II | L | 3-2 |
| USA USL League One | 2019/09/06 23:30 | Orlando City II v North Texas SC | L | 1-3 |
| USA USL League One | 2019/08/25 02:30 | FC Tucson v Orlando City II | L | 3-1 |
| USA USL League One | 2019/08/16 23:30 | Orlando City II v Lansing Ignite FC | L | 1-2 |
| USA USL League One | 2019/08/03 23:00 | Lansing Ignite FC v Orlando City II | L | 3-0 |