[29] Richmond Kickers 3-2 Penn FC [26] 2018-08-18 23:00
Weather: Good Stadium: City Stadium Pitch: Excellent Round: 1
Head to Head
| USA USL Championship | 2018/07/09 23:00 | Penn FC v Richmond Kickers | W | 1-2 |
| USA USL Championship | 2018/06/12 23:00 | Penn FC v Richmond Kickers | L | 2-1 |
| USA US Open Cup | 2018/05/23 23:00 | Richmond Kickers v Penn FC | W | 3-2 |
| USA USL Championship | 2017/07/15 23:00 | Penn FC v Richmond Kickers | L | 1-0 |
| USA USL Championship | 2017/05/13 23:00 | Richmond Kickers v Penn FC | D | 0-0 |
| USA USL Championship | 2017/03/25 21:00 | Richmond Kickers v Penn FC | W | 1-0 |
| USA USL Championship | 2016/07/08 23:00 | Penn FC v Richmond Kickers | W | 0-3 |
| USA USL Championship | 2016/03/26 21:00 | Richmond Kickers v Penn FC | W | 3-1 |