Home History
| USA NISA Legends Cup | 2021/04/26 00:00 | Chattanooga FC v Detroit City FC | W | 0-3 |
| USA NISA Legends Cup | 2021/04/23 00:00 | Detroit City FC v San Diego 1904 FC | W | 1-0 |
| USA NISA Legends Cup | 2021/04/16 16:00 | Detroit City FC v Stumptown Athletic FC | W | 2-0 |
| USA NISA Legends Cup | 2021/04/13 21:00 | Detroit City FC v California Utd Strikers | D | 0-0 |
| USA NISA | 2020/10/02 22:00 | Oakland Roots v Detroit City FC | W | 1-2 |
| USA NISA | 2020/10/01 00:02 | Detroit City FC v LA Force | W | 1-0 |
| USA NISA | 2020/09/28 00:00 | Detroit City FC v New Amsterdam FC | W | 4-2 |
| USA NISA | 2020/09/24 21:00 | Oakland Roots v Detroit City FC | W | 1-2 |
Away History
| USA NISA Legends Cup | 2021/04/22 18:00 | California Utd Strikers v Maryland Bobcats FC | L | 3-2 |
| USA NISA Legends Cup | 2021/04/20 00:00 | Michigan Stars v Maryland Bobcats FC | D | 1-1 |
| USA NISA Legends Cup | 2021/04/16 21:00 | Maryland Bobcats FC v San Diego 1904 FC | L | 1-2 |
| World Club Friendlies | 2020/10/25 00:56 | Chattanooga FC v Maryland Bobcats FC | W | 0-1 |
| USA NISA Independent Cup | 2020/08/10 00:06 | Maryland Bobcats FC v New York Cosmos | D | 1-1 |
| USA NISA Independent Cup | 2020/08/03 00:45 | FC Baltimore v Maryland Bobcats FC | D | 1-1 |