Stadium: Grandstand Round: 27 Ground: Clay
| Challenger Todi | 2023/08/16 17:15 | Enrico Dalla Valle v Felix Gill | 7-5,4-6,4-6 |
| Challenger Todi | 2023/08/15 14:00 | Felix Gill v Francesco Forti | 7-6,4-6,7-6 |
| Challenger Todi | 2023/08/14 11:45 | Mathys Erhard v Felix Gill | 6-1,3-6,0-6 |
| Challenger Todi | 2023/08/13 14:40 | Felix Gill v Juan Bautista Otegui | 1-6,6-3,6-3 |
| Challenger Meerbusch | 2023/08/09 09:25 | Daniel Rincon v Felix Gill | 6-4,6-2 |
| Challenger Meerbusch | 2023/08/08 09:00 | Felix Gill v Miguel Damas | 6-3,1-6,6-3 |
| Challenger Meerbusch | 2023/08/07 11:55 | Felix Gill v Pedro Vives Marcos | 7-6,7-6 |
| ITF M25 Denia | 2023/07/27 08:00 | Felix Gill v Iker Urribarrens | 3-6,6-2,3-6 |
| Challenger Todi | 2023/08/16 19:45 | Giovanni Fonio v Julian Ocleppo | 6-3,6-7,6-4 |
| Challenger Todi | 2023/08/15 09:55 | Giovanni Fonio v Orlando Luz | 7-6,6-4 |
| Challenger Cordenons | 2023/08/08 08:00 | Giovanni Fonio v Nicholas David Ionel | 3-6,7-5,5-7 |
| Challenger Liberec | 2023/07/31 14:00 | Giovanni Fonio v Norbert Gombos | 6-7,4-6 |
| Challenger Zug | 2023/07/23 09:00 | Giovanni Fonio v Dylan Dietrich | 3-6,3-6 |
| Challenger Tampere | 2023/07/17 15:30 | Giovanni Fonio v Vit Kopriva | 4-6,6-7 |
| Challenger Troyes | 2023/07/05 10:20 | Giovanni Fonio v Moez Echargui | 6-3,6-2 |
| Challenger Troyes | 2023/07/03 15:30 | Marco Trungelliti v Giovanni Fonio | 4-6,2-6 |