| Challenger Florianopolis | 03/31 14:30 | 14 | [203] Kelsey Stevenson v Franco Roncadelli [443] | 4-6,4-6 | |
| Challenger Kigali | 03/04 08:00 | 19 | Akram El Sallaly v Kelsey Stevenson | 7-6,7-6 | |
| Challenger Kigali | 03/03 09:50 | 14 | Ren Nakamura v Kelsey Stevenson | 6-7,3-6 | |
| Challenger Kigali | 02/25 12:00 | 14 | Kelsey Stevenson v Lucas Bouquet | 1-6,4-6 | |
| ITF M25 Hammamet | 01/28 08:00 | 62 | Ferdinand Kloesters v Kelsey Stevenson | 6-4,6-2 | |
| Challenger Drummondville | 11/12 22:55 | 14 | Kelsey Stevenson v Patrick Brady | 6-7,4-6 | |
| Challenger Calgary | 11/05 17:00 | 14 | Kelsey Stevenson v Patrick Brady | 2-6,1-6 | |
| Challenger Winnipeg | 08/13 16:00 | 14 | [375] Aidan Mayo v Kelsey Stevenson [241] | 6-4,6-4 | |
| Challenger Medellin | 06/26 18:00 | 14 | [362] Tristan McCormick v Kelsey Stevenson [207] | 6-4,7-6 | |
| ITF M25 Jakarta | 04/18 06:10 | 44 | Yuta Kawahashi v Kelsey Stevenson | Retired | |
| ITF M25 Jakarta | 04/17 07:55 | 44 | Blake Bayldon v Kelsey Stevenson | 6-7,1-6 | |
| ITF M25 Jakarta | 04/10 06:05 | 44 | Corban Crowther v Kelsey Stevenson | 7-5,6-3 | |
| ITF M15 Singapur | 04/05 05:25 | 25 | Kelsey Stevenson v Seon Yong Han | 6-2,4-6,2-6 | |
| ITF M25 Lucknow | 03/20 04:30 | 44 | Kelsey Stevenson v Yash Chaurasia | 1-6,6-7 | |
| ITF M15 Sharm El Sheikh | 12/22 08:00 | 26 | [469] Marat Sharipov v Kelsey Stevenson [271] | Retired | |
| ITF M15 Sharm El Sheikh | 12/21 08:00 | 25 | Kelsey Stevenson v Petr Bar Biryukov | 6-2,6-2 | |
| ITF M15 Sharm El Sheikh | 12/14 10:30 | 25 | [275] Kelsey Stevenson v Samuel Vincent Ruggeri [432] | 1-6,5-7 | |
| ITF M15 Sharm El Sheikh | 12/08 08:00 | 26 | Amr Elsayed v Kelsey Stevenson | Retired | |
| ITF M15 Sharm El Sheikh | 12/07 11:35 | 25 | Kelsey Stevenson v Matteo Fondriest | 6-2,6-0 | |
| Challenger Drummondville | 11/13 15:00 | 14 | Kelsey Stevenson v Roy Smith | 3-6,4-6 | |
| Challenger Calgary | 11/06 19:30 | 14 | [322] Maxmilian Neuchrist v Kelsey Stevenson [281] | 7-5,6-2 | |
| Challenger Brest | 10/23 16:25 | 14 | [345] Kenny de Schepper v Kelsey Stevenson [289] | 6-3,6-2 | |
| Challenger Hamburk | 10/16 18:00 | 14 | [285] Kelsey Stevenson v Matteo Martineau [456] | 3-6,3-6 | |
| Challenger Istanbul | 09/12 12:35 | 19 | [479] Dominik Palan v Kelsey Stevenson [302] | 7-6,6-2 | |
| Challenger Istanbul | 09/11 11:35 | 14 | Adrian Oetzbach v Kelsey Stevenson | 6-4,5-7,6-7 | |
| ITF M25 Sintra | 09/08 09:30 | 26 | Adria S Barrera v Kelsey Stevenson | 7-5,6-2 | |
| ITF M25 Sintra | 09/07 12:55 | 25 | Nuno Pinheiro v Kelsey Stevenson | 4-6,3-6 | |
| Challenger Granby | 08/22 17:45 | 19 | [326] Kelsey Stevenson v Luke Saville [92] | 3-6,6-7 | |
| Challenger Granby | 08/21 17:15 | 14 | Kelsey Stevenson v Aurel Ciocanu | 3-6,6-4,6-1 | |
| ATP Montreal | 08/06 15:00 | 14 | [55] Fabio Fognini v Kelsey Stevenson [329] | 6-3,6-1 |