Stadion: Court 2 Round: 54 Ground: Clay
| ITF - M15 - Kampala | 2019/05/20 14:35 | Gokul Suresh v Kevin Cheruiyot | 6-4,7-6 |
| ITF - M15 - Kampala | 2019/05/13 10:00 | Kevin Cheruiyot v Philipp Dittmer | 7-5,6-7,5-10 |
| ITF - M15 - Kampala | 2019/05/07 08:30 | Niklas Johansson v Kevin Cheruiyot | 6-2,6-1 |
| Challenger - Busan | 2019/05/06 08:00 | Ahmed Choudhary v Kevin Cheruiyot | 4-6,6-1,5-10 |
| Challenger - Busan | 2019/05/06 05:30 | Kevin Cheruiyot v Dipanshu Garg | 6-4,6-3 |
| ITF - Australien F7 | 2018/09/29 00:00 | Winter Meagher v Kevin Cheruiyot | 6-1,6-3 |
| ITF - Australien F6 | 2018/09/22 00:30 | Kevin Cheruiyot v Beauregard Treyz | 2-6,2-6 |
| ITF - Australien F5 | 2018/09/15 00:30 | Corey Gaal v Kevin Cheruiyot | 6-0,6-2 |