Stadium: Court 1 Round: 25 Ground: Clay
| ITF M15 Sofia | 2023/07/03 11:30 | Viktor Jovic v Antonio Massara | 6-4,4-6,7-10 |
| ITF M15 Sofia | 2023/07/03 06:30 | Nikola Kolyachev v Antonio Massara | 3-6,7-6,12-14 |
| ITF M15 Duffel | 2023/06/12 12:00 | Sander Jong v Antonio Massara | 6-2,6-2 |
| ITF M15 Duffel | 2023/06/11 16:00 | Hoogland, Joris v Antonio Massara | 2-6,1-6 |
| ITF - M15 Porec | 2023/03/09 13:10 | Antonio Massara v Prechtel, Sebastian | 1-6,6-3,3-6 |
| ITF - M15 Porec | 2023/03/08 11:40 | Antonio Massara v Sodan, Ivan | 6-3,2-6,6-3 |
| ITF - M15 Porec | 2023/03/07 10:30 | Luca Matteo Sobbe v Antonio Massara | 6-7,6-1,8-10 |
| ITF - M15 Porec | 2023/03/06 12:25 | Twan Van Zijl v Antonio Massara | 1-6,1-6 |
| ITF - M15 Constanta | 2023/06/01 08:00 | Ivanov, Simon Anthony v Ignacio Carou | 6-4,6-2 |
| ITF - M15 Constanta | 2023/05/30 11:00 | Ivanov, Simon Anthony v Kai Lemstra | 6-2,6-2 |
| ITF M15 Pazardzhik | 2023/05/26 07:00 | Ivanov, Simon Anthony v Corentin Denolly | 3-6,7-6,2-6 |
| ITF M15 Pazardzhik | 2023/05/25 08:30 | Ivanov, Simon Anthony v Luigi Sorrentino | 6-1,6-3 |
| ITF M15 Pazardzhik | 2023/05/24 09:30 | Ivanov, Simon Anthony v Gabriele Maria Noce | 6-4,3-6,7-6 |
| ITF M15 Pazardzhik | 2023/05/21 07:00 | Ivanov, Simon Anthony v Roncalli, Simone | 3-6,6-3,4-6 |
| ITF M15 Pazardzhik | 2023/05/20 09:00 | Marco Miceli v Ivanov, Simon Anthony | 0-6,1-6 |
| ITF M15 Pazardzhik | 2023/05/19 10:10 | Leonardo Rossi v Ivanov, Simon Anthony | 4-6,4-6 |