Stadium: Centre Court Round: 54 Ground: Clay
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/14 06:00 | Chaukulkar, Tejas v Rishi Reddy | 5-7,6-4,8-10 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/14 06:00 | Chaukulkar, Tejas v Rishi Reddy | 5-7,6-4,8-10 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/13 09:30 | Chaukulkar, Tejas v Chilakalapudi, Tarun Anirudh | 6-4,6-2 |
| Challenger - Pune | 2018/11/17 04:30 | Vilardo, Francesco v Chaukulkar, Tejas | 6-7,6-1,6-0 |
| ITF Egypt F20 | 2018/09/26 10:00 | Chaukulkar, Tejas v Bertuccioli, Federico | 6-2,2-6,5-7 |
| Egypt F19, Singles Qualifying | 2018/09/18 08:00 | Chaukulkar, Tejas v Exposito, Adrian | 4-6,2-6 |
| Egypt F18, Singles Qualifying | 2018/09/11 07:30 | Roncalli, Simone v Chaukulkar, Tejas | 6-3,6-1 |
| ITF Germany F11 | 2018/08/08 10:00 | Chaukulkar, Tejas v Kaczynski, Kevin | 3-6,6-4,1-6 |
| ITF Germany F11 | 2018/08/06 11:00 | Milan Welte v Chaukulkar, Tejas | 2-6,3-6 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/17 10:00 | Carr, Simon v Rishi Reddy | 6-1,6-2 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/16 11:45 | Rishi Reddy v Niki Kaliyanda Poonacha | 6-2,6-4 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/15 15:45 | Samaha, Giovani v Rishi Reddy | 6-4,6-7,4-6 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/14 06:00 | Chaukulkar, Tejas v Rishi Reddy | 5-7,6-4,8-10 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/08 10:15 | Nedelko, Ivan v Rishi Reddy | 7-5,6-3 |
| Antalya, Singles Qualifying W-ITF-TUR-18A | 2019/05/06 08:00 | Rishi Reddy v Yego, Ibrahim Kibet | 3-6,6-3,12-10 |
| ITF Egypt F30 | 2018/12/03 08:00 | Uspensky, Dennis v Rishi Reddy | 6-0,6-1 |
| ITF Egypt F30 | 2018/12/01 08:00 | Defilippis, Sebastian v Rishi Reddy | 2-6,0-6 |