Stadium: Court 3 Round: 44 Ground: Carpet indoor
| Challenger - Pune | 2019/11/12 05:30 | Kaza, Vinayak Sharma v Chaukulkar, Tejas | 7-6,6-7,6-4 |
| Challenger - Pune | 2019/11/11 05:30 | Yash Chaurasia v Chaukulkar, Tejas | 3-6,4-6 |
| ITF M15 Trier | 2019/08/13 07:30 | Chaukulkar, Tejas v Link, Joel Vincent | 6-2,2-6,11-13 |
| Wetzlar, Singles Qualifying M-ITF-GER-11A | 2019/08/05 12:00 | Chaukulkar, Tejas v Batlle, Carles | 6-3,0-6,5-10 |
| Wetzlar, Singles Qualifying M-ITF-GER-11A | 2019/08/05 08:00 | Chaukulkar, Tejas v Mortier, Sebastian | 6-3,6-4 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/22 06:00 | Carr, Simon v Chaukulkar, Tejas | 6-1,6-2 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/21 08:50 | Chaukulkar, Tejas v Rishi Reddy | 3-6,6-4,7-10 |
| Kampala, Singles Qualifying M-ITF-UGA-02A | 2019/05/14 06:00 | Chaukulkar, Tejas v Rishi Reddy | 5-7,6-4,8-10 |
| ITF - M15 Antalya | 2019/12/17 07:00 | Karlo Cubelic v Luca Castagnola | 6-1,6-7,6-10 |
| ITF - M15 Antalya | 2019/12/16 08:00 | Karlo Cubelic v Yehayan, Mikhail | 6-1,6-0 |
| Antalya, Qualifications Simples M-ITF-TUR-33A | 2019/12/09 07:00 | Karlo Cubelic v Kuzey Cekirge | 4-6,6-7 |
| ITF M15 Cancun | 2019/11/21 17:10 | Karlo Cubelic v Brymer, Gage | 2-6,2-6 |
| ITF M15 Cancun | 2019/11/20 17:40 | Karlo Cubelic v Stefani Figlia, B. | 6-3,6-1 |
| ITF M15 Cancun | 2019/11/19 14:00 | Alex Hernandez v Karlo Cubelic | 3-6,6-2,1-10 |
| ITF M15 Cancun | 2019/11/18 13:45 | Alvarez Vergara, Camilo Andres v Karlo Cubelic | 0-6,0-6 |
| ITF M15 Cancun | 2019/11/17 15:30 | Lage Castelan, Lance Amaury v Karlo Cubelic | 0-6,0-6 |