Stadium: Court 2 Round: 54 Ground: Clay
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/20 14:35 | Suresh, Gokul v Cheruiyot, Kevin | 6-4,7-6 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/13 10:00 | Cheruiyot, Kevin v Dittmer, Philipp | 7-5,6-7,5-10 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/07 08:30 | Johansson, Niklas v Cheruiyot, Kevin | 6-2,6-1 |
| Antalya, Singles Qualifying W-ITF-TUR-18A | 2019/05/06 08:00 | Choudhary, Ahmed v Cheruiyot, Kevin | 4-6,6-1,5-10 |
| Antalya, Singles Qualifying W-ITF-TUR-18A | 2019/05/06 05:30 | Cheruiyot, Kevin v Garg, Dipanshu | 6-4,6-3 |
| ITF Australia F7 | 2018/09/29 00:00 | Winter Meagher v Cheruiyot, Kevin | 6-1,6-3 |
| ITF Australia F6 | 2018/09/22 00:30 | Cheruiyot, Kevin v Treyz, Beauregard | 2-6,2-6 |
| ITF Australia F5 | 2018/09/15 00:30 | Corey Gaal v Cheruiyot, Kevin | 6-0,6-2 |