Stadium: Court 7 Round: 14 Ground: Clay
| Challenger Grodzisk Mazowiecki | 2023/08/14 10:50 | Niki Kaliyanda Poonacha v David Poljak | 3-6,2-6 |
| Challenger Grodzisk Mazowiecki | 2023/08/13 14:50 | Saba Purtseladze v Niki Kaliyanda Poonacha | 4-6,2-6 |
| Challenger Cordenons | 2023/08/06 10:05 | Alex Barrena v Niki Kaliyanda Poonacha | 6-3,7-6 |
| Challenger Porto | 2023/07/31 12:40 | Kenny de Schepper v Niki Kaliyanda Poonacha | 6-2,6-4 |
| Challenger Porto | 2023/07/30 17:20 | Niki Kaliyanda Poonacha v Luca Potenza | 7-5,6-1 |
| Challenger Astana | 2023/07/25 09:45 | Rubin Statham v Niki Kaliyanda Poonacha | 6-1,6-4 |
| Challenger Astana | 2023/07/24 06:50 | Niki Kaliyanda Poonacha v Arslanbek Aitkulov | 6-1,6-3 |
| Challenger Astana | 2023/07/23 08:40 | Niki Kaliyanda Poonacha v Mustafa Dustov | 6-3,6-2 |
| Challenger Todi | 2023/08/13 10:55 | Miljan Zekic v Gabriele Piraino | 7-5,7-5 |
| Challenger San Marino | 2023/07/30 12:05 | Gabriele Piraino v Enrico Dalla Valle | 5-7,1-6 |
| ITF - Perugia M15 | 2023/07/28 15:00 | Manuel Mazza v Gabriele Piraino | 6-3,6-4 |
| ITF - Perugia M15 | 2023/07/27 13:00 | Niccolo Catini v Gabriele Piraino | 2-6,2-6 |
| ITF - Perugia M15 | 2023/07/26 17:00 | Luciano Carraro v Gabriele Piraino | 2-6,2-6 |
| Challenger Trieste | 2023/07/18 09:00 | Zdenek Kolar v Gabriele Piraino | 7-6,2-6,6-3 |
| Challenger San Benedetto | 2023/07/11 17:45 | Gabriele Piraino v Ricardas Berankis | 6-7,4-6 |
| Challenger San Benedetto | 2023/07/10 11:35 | Dmitry Popko v Gabriele Piraino | 6-3,6-2 |