Stadium: Court 5 Round: 62 Ground: Clay
| ITF M15 Cairo | 2021/09/20 08:00 | O'Jon, Ian v Lucio Carnevalle | 1-6,1-6 |
| ITF M15 Cairo | 2021/09/19 07:30 | O'Jon, Ian v Elkamony, Anwar | 6-1,6-0 |
| ITF M15 Cairo | 2021/09/13 08:00 | O'Jon, Ian v Lucio Carnevalle | 6-4,3-6,6-10 |
| ITF M15 Cairo | 2021/09/12 11:00 | O'Jon, Ian v Dacenko, Artem | 6-4,6-2 |
| ITF M15 Cancun | 2019/05/06 13:30 | Shamma, Nicholas v O'Jon, Ian | 6-3,5-7,10-8 |
| ITF South Africa F3 Qual | 2018/12/02 11:30 | O'Jon, Ian v van Meter, Joseph W | 6-3,3-6,4-6 |
| ITF South Africa F3 Qual | 2018/12/01 10:30 | O'Jon, Ian v Du Toit, Daniel | 6-4,6-3 |
| South Africa F2, Singles | 2018/11/26 12:00 | Patrick Foley v O'Jon, Ian | 6-4,2-6,6-3 |
| ITF M15 Cairo | 2021/09/19 13:30 | Chilakalapudi, Tarun Anirudh v Sean Hess | 0-6,0-6 |
| ITF M15 Cairo | 2021/09/14 07:00 | Adrian Oetzbach v Chilakalapudi, Tarun Anirudh | 6-0,6-0 |
| ITF M15 Cairo | 2021/09/12 07:00 | Chilakalapudi, Tarun Anirudh v Noikor, Noppadol | 1-6,6-4,10-8 |
| ITF M25 Ueberlingen | 2021/08/16 13:45 | Santibanez, Sebastian v Chilakalapudi, Tarun Anirudh | 6-3,6-2 |
| ITF M15 Indore | 2021/03/08 08:30 | Chilakalapudi, Tarun Anirudh v Baskov, Dmitrii | 2-6,2-6 |
| ITF M15 Indore | 2021/03/08 04:45 | Sood, Chandril v Chilakalapudi, Tarun Anirudh | 6-4,3-6,7-10 |
| ITF M15 Indore | 2021/03/07 03:30 | Peranamallur, Chandrasekhar Vignesh v Chilakalapudi, Tarun Anirudh | 3-6,6-7 |
| ITF M15 Lucknow | 2021/02/28 10:15 | Prashanth, N. Vijay Sundar v Chilakalapudi, Tarun Anirudh | 6-3,6-1 |