Stadium: Court 7 Round: 25 Ground: Clay
| ITF M15 Las Palmas | 2019/05/08 08:00 | Jotovski, Tomislav v Jaimee Floyd Angele | 5-7,3-6 |
| ITF M15 Las Palmas | 2019/04/30 10:00 | Jotovski, Tomislav v Largo, Hugo | 5-7,2-6 |
| ITF - M15 Antalya | 2019/04/04 08:40 | Jotovski, Tomislav v Dan Alexandru Tomescu | 2-6,4-6 |
| ITF - M15 Antalya | 2019/04/03 08:55 | Jotovski, Tomislav v Vlad Andrei Dancu | 1-6,6-3,7-6 |
| ITF - M15 Antalya | 2019/03/26 11:55 | Sengul, Bora v Jotovski, Tomislav | 4-6,4-6 |
| ITF - M15 Antalya | 2019/03/19 07:15 | Dzhanashia, Shalva v Jotovski, Tomislav | 6-7,6-4,6-4 |
| ITF - M15 Antalya | 2019/03/12 07:15 | Jotovski, Tomislav v Gomar Monio, Luis | 2-6,3-6 |
| ITF - M15 Antalya | 2019/03/11 07:15 | Jotovski, Tomislav v Bingyu Yu | 6-3,6-4 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/05/20 13:00 | Hersey, Jake v Iamachkine, Pedro | 6-3,7-5 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/05/20 08:00 | Hersey, Jake v Marouani, Elyes | 6-1,6-3 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/22 08:00 | Hersey, Jake v Diego F Flores | 1-6,1-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/15 08:00 | Fattar, Anas v Hersey, Jake | 7-5,6-2 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/18 12:30 | Battaglino, Stefano v Hersey, Jake | 6-2,6-7,10-7 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/18 08:00 | Hersey, Jake v Cordonnier, Gregorio | 6-4,0-6,12-10 |
| ITF M15 Palmanova | 2019/01/21 11:00 | Tashi, Vullnet v Hersey, Jake | 6-7,7-6,10-5 |
| ITF - M15 Manacor | 2019/01/16 08:30 | Ehrat, Sandro v Hersey, Jake | 6-4,6-1 |