Stadium: Court 1 Round: 28 Ground: Hardcourt outdoor
| ITF M15 New Delhi | 2021/04/02 05:30 | Kotzen, Alexander v Oliver Crawford | 4-6,5-7 |
| ITF M15 New Delhi | 2021/04/01 07:50 | Fardeen Qamar v Oliver Crawford | 2-6,1-6 |
| ITF M15 New Delhi | 2021/03/31 07:15 | Ishaque Eqbal v Oliver Crawford | 7-6,1-6,3-6 |
| ITF M15 Pune | 2021/03/28 04:30 | Oliver Crawford v Khan, Zane | 6-3,6-0 |
| ITF M15 Pune | 2021/03/27 07:00 | Manish Sureshkumar v Oliver Crawford | 4-6,2-6 |
| ITF M15 Pune | 2021/03/26 06:00 | Oliver Crawford v Arjun Kadhe | 6-3,7-6 |
| ITF M15 Pune | 2021/03/25 10:55 | Oliver Crawford v Dev Javia | 4-6,6-1,6-2 |
| ITF M15 Pune | 2021/03/24 05:40 | Oliver Crawford v Sharma, Atharva | 6-1,6-0 |
| ITF M15 New Delhi | 2021/04/02 05:30 | Zsombor Velcz v Carr, Simon | 3-6,6-2,3-6 |
| ITF M15 New Delhi | 2021/04/01 06:40 | Brugnerotto, Marco v Carr, Simon | 4-6,3-6 |
| ITF M15 New Delhi | 2021/03/31 05:50 | Goveas, Aryan v Carr, Simon | 0-6,1-6 |
| ITF M15 Pune | 2021/03/26 04:30 | Jonathan Mridha v Carr, Simon | 7-5,2-6,6-1 |
| ITF M15 Pune | 2021/03/25 06:50 | Bergevi, Filip v Carr, Simon | 2-6,6-7 |
| ITF M15 Pune | 2021/03/24 10:00 | Sunish, Dhruv v Carr, Simon | 2-6,6-3,4-6 |
| ITF - M15 Monastir | 2021/03/18 08:30 | Savva Polukhin v Carr, Simon | 7-5,6-1 |
| ITF - M15 Monastir | 2021/03/17 08:20 | Alex Barrena v Carr, Simon | 2-6,3-6 |