| Challenger Champaign | 11/18 19:35 | 28 | [169] Titouan Droguet v Alex Michelsen [99] | 6-2,4-6,3-6 | |
| Challenger Champaign | 11/17 17:00 | 27 | [266] Martin Damm v Alex Michelsen [99] | 1-6,6-1,4-6 | |
| Challenger Champaign | 11/16 18:20 | 26 | [328] Sebastian Fanselow v Alex Michelsen [99] | 3-6,2-6 | |
| Challenger Champaign | 11/15 01:25 | 25 | [289] Bernard Tomic v Alex Michelsen [99] | 4-6,0-6 | |
| Challenger Knoxville | 11/12 18:00 | 29 | [183] Denis Kudla v Alex Michelsen [114] | 5-7,6-4,2-6 | |
| Challenger Knoxville | 11/11 18:25 | 28 | [114] Alex Michelsen v Tennys Sandgren [267] | 6-2,2-6,6-4 | |
| Challenger Knoxville | 11/10 19:05 | 27 | [497] Nishesh Basavareddy v Alex Michelsen [114] | 3-6,3-6 | |
| Challenger Knoxville | 11/08 17:50 | 26 | [322] Gabriel Debru v Alex Michelsen [114] | 3-6,6-3,4-6 | |
| Challenger Knoxville | 11/07 00:55 | 25 | [292] Bernard Tomic v Alex Michelsen [114] | 6-4,6-7,4-6 | |
| Challenger Charlottesville | 10/31 18:45 | 25 | [432] Cannon Kingsley v Alex Michelsen [112] | 7-5,6-3 | |
| Challenger Fairfield | 10/13 18:30 | 27 | Alex Michelsen v Nishesh Basavareddy | 3-6,3-6 | |
| Challenger Fairfield | 10/12 17:00 | 26 | [110] Alex Michelsen v Thai-Son Kwiatkowski [426] | 6-3,6-4 | |
| Challenger Fairfield | 10/10 18:50 | 25 | [110] Alex Michelsen v Aziz Dougaz [248] | 2-6,7-6,6-0 | |
| Challenger Tiburon | 10/05 23:30 | 26 | [110] Alex Michelsen v Thai-Son Kwiatkowski [426] | 6-4,4-6,3-6 | |
| Challenger Tiburon | 10/03 20:20 | 25 | Alex Michelsen v Brayden Schnur | 6-7,6-3,6-4 | |
| Challenger Cary | 09/16 21:00 | 28 | [207] Zachary Svajda v Alex Michelsen [117] | 6-3,7-5 | |
| Challenger Cary | 09/15 21:00 | 27 | [228] Guido Andreozzi v Alex Michelsen [117] | 3-6,5-7 | |
| Challenger Cary | 09/13 23:20 | 26 | [426] Strong Kirchheimer v Alex Michelsen [117] | 3-6,1-6 | |
| Challenger Cary | 09/12 18:45 | 25 | [392] Maxime Janvier v Alex Michelsen [117] | 7-5,6-7,3-6 | |
| US Open | 08/31 20:00 | 24 | [25] Nicolas Jarry v Alex Michelsen [127] | 4-6,6-3,6-3,6-3 | |
| US Open | 08/29 16:40 | 23 | [88] Albert Ramos-Vinolas v Alex Michelsen [127] | 4-6,3-6,4-6 | |
| ATP Winston-Salem | 08/24 01:50 | 26 | [34] Laslo Djere v Alex Michelsen [133] | 6-4,6-4 | |
| ATP Winston-Salem | 08/22 18:00 | 25 | [133] Alex Michelsen v Sebastian Ofner [59] | 7-6,7-5 | |
| ATP Winston-Salem | 08/20 22:30 | 24 | [138] Alex Michelsen v Juan Pablo Varillas [74] | 6-3,6-7,6-0 | |
| Challenger Stanford | 08/15 20:35 | 26 | [114] Borna Gojo v Alex Michelsen [138] | 4-6,6-4,7-6 | |
| Challenger Stanford | 08/14 05:00 | 25 | Alex Michelsen v Seongchan Hong | 4-6,6-2,6-0 | |
| ATP Atlanta | 07/25 20:10 | 25 | [105] Maxime Cressy v Alex Michelsen [140] | 6-3,6-3 | |
| ATP Newport | 07/23 18:30 | 29 | [190] Alex Michelsen v Adrian Mannarino [38] | 2-6,4-6 | |
| ATP Newport | 07/22 19:20 | 28 | [126] John Isner v Alex Michelsen [190] | 6-7,4-6 | |
| ATP Newport | 07/21 17:00 | 27 | [59] Mackenzie McDonald v Alex Michelsen [190] | 3-6,3-6 |