Stadium: Court 1 Round: 24 Ground: Hardcourt indoor
| Challenger Drummondville | 2020/02/18 15:00 | Lloyd Glasspool v Vasil Kirkov | 6-7,6-3,0-6 |
| ITF M25 Rancho Santa Fe | 2020/01/15 17:25 | Juan Manuel Cerundolo v Lloyd Glasspool | 1-6,6-2,6-4 |
| Challenger Ann Arbor | 2020/01/06 15:25 | Lloyd Glasspool v John McNally | 4-6,1-6 |
| Challenger Champaign | 2019/11/14 19:25 | Lloyd Glasspool v Blaz Kavcic | 5-7,6-7 |
| Challenger Champaign | 2019/11/12 20:40 | Kaichi Uchida v Lloyd Glasspool | 5-7,6-7 |
| Challenger Champaign | 2019/11/11 18:15 | Lloyd Glasspool v Michael Geerts | 3-6,6-3,6-2 |
| Challenger Knoxville | 2019/11/06 16:30 | Lloyd Glasspool v Brandon Nakashima | 6-7,6-3,6-7 |
| Challenger Knoxville | 2019/11/04 15:00 | Lloyd Glasspool v Strong Kirchheimer | 1-6,5-7 |
| ITF M15 East Lansing | 2019/11/23 18:50 | Michael Geerts v Cannon Kingsley | 6-7,6-4,7-6 |
| ITF M15 East Lansing | 2019/11/22 17:00 | Cannon Kingsley v Jacob Dunbar | 6-3,5-7,6-4 |
| ITF M15 East Lansing | 2019/11/20 21:15 | Cannon Kingsley v Mattias Siimar | 7-5,6-2 |
| Challenger Charlottesville | 2019/10/28 14:00 | Liam Caruana v Cannon Kingsley | 6-3,7-6 |
| Challenger Columbus 3 | 2019/09/17 17:45 | Thai-Son Kwiatkowski v Cannon Kingsley | 3-6,6-4,6-3 |
| Challenger Columbus 3 | 2019/09/16 20:10 | Evan Song v Cannon Kingsley | 4-6,6-2,2-6 |
| ITF M25 Champaign | 2019/07/26 21:00 | Cannon Kingsley v Aleksandar Kovacevic | 4-6,4-6 |
| ITF M25 Champaign | 2019/07/25 17:00 | Cannon Kingsley v Michael Shabaz | 6-7,6-2,6-4 |