Estadio: Aquinas College Athletic Field Round: 1
| EE.UU. - USL League Two | 2023/07/01 23:30 | Oakland County FC v Midwest United | L | 4-3 |
| EE.UU. - USL League Two | 2023/06/29 23:00 | Midwest United v AFC Ann Arbor | W | 2-1 |
| EE.UU. - USL League Two | 2023/06/22 00:00 | Midwest United v Flint City Bucks | L | 0-1 |
| EE.UU. - USL League Two | 2023/06/17 21:00 | South Bend Lions v Midwest United | D | 0-0 |
| EE.UU. - USL League Two | 2023/06/14 23:00 | Lansing City Football v Midwest United | L | 3-2 |
| EE.UU. - USL League Two | 2023/06/07 23:00 | Kalamazoo FC v Midwest United | D | 1-1 |
| EE.UU. - USL League Two | 2023/06/03 23:00 | AFC Ann Arbor v Midwest United | L | 2-1 |
| EE.UU. - USL League Two | 2023/06/01 00:00 | Midwest United v Kalamazoo FC | W | 4-2 |