| Challenger Bergamo | 10/30 15:30 | 25 | [186] Matteo Gigante v Alex Molcan [119] | 2-6,2-6 | |
| Challenger Olbia | 10/17 11:45 | 25 | [188] Matteo Gigante v Arthur Cazaux [123] | 2-6,2-6 | |
| Challenger Lisbon | 10/02 13:55 | 25 | [185] Matteo Gigante v Franco Agamenone [204] | 4-6,6-7 | |
| Challenger Braga | 09/28 12:00 | 26 | [185] Matteo Gigante v Benjamin Hassan [208] | 4-6,6-1,1-6 | |
| Challenger Braga | 09/26 11:00 | 25 | [173] Matteo Gigante v Edoardo Lavagno [227] | 6-3,6-4 | |
| Challenger Genoa | 09/05 20:15 | 25 | [169] Matteo Gigante v Stefano Napolitano [297] | 3-6,1-6 | |
| Challenger Como | 08/29 16:30 | 25 | [169] Matteo Gigante v Stefano Napolitano [297] | 3-6,0-6 | |
| US Open | 08/23 23:15 | 14 | Eliot Spizzirri v Matteo Gigante | 6-4,6-7,6-1 | |
| Challenger Cordenons | 08/13 16:00 | 29 | [251] Lukas Neumayer v Matteo Gigante [202] | 0-6,2-6 | |
| Challenger Cordenons | 08/12 15:00 | 28 | [202] Matteo Gigante v Enrico Dalla Valle [390] | 7-6,6-2 | |
| Challenger Cordenons | 08/11 11:00 | 27 | [247] Hernan Casanova v Matteo Gigante [202] | 1-6,6-7 | |
| Challenger Cordenons | 08/10 12:00 | 26 | [482] Blaz Rola v Matteo Gigante [202] | 5-7,2-6 | |
| Challenger Cordenons | 08/08 17:30 | 25 | [404] Vladyslav Orlov v Matteo Gigante [202] | 7-6,4-6,4-6 | |
| Challenger Zug | 07/28 13:00 | 27 | [209] Matteo Gigante v Joris De Loore [202] | 6-3,6-7,4-6 | |
| Challenger Zug | 07/27 08:30 | 26 | [174] Dimitar Kuzmanov v Matteo Gigante [209] | 4-6,6-7 | |
| Challenger Zug | 07/26 13:45 | 25 | [167] Dalibor Svrcina v Matteo Gigante [209] | 1-6,7-6,3-6 | |
| Challenger Trieste | 07/19 14:45 | 26 | [93] Fabian Marozsan v Matteo Gigante [218] | 7-6,3-6,7-5 | |
| Challenger Trieste | 07/18 08:00 | 25 | [329] Clement Tabur v Matteo Gigante [218] | 4-6,7-6,3-6 | |
| Challenger San Benedetto | 07/11 13:50 | 25 | [264] Michael Geerts v Matteo Gigante [256] | 4-6,6-4,6-4 | |
| Challenger Milan | 07/09 14:30 | 29 | [115] Facundo D Acosta v Matteo Gigante [256] | 6-3,6-3 | |
| Challenger Milan | 07/08 15:45 | 28 | [256] Matteo Gigante v Luciano Darderi [229] | 6-4,3-6,7-5 | |
| Challenger Milan | 07/07 12:15 | 27 | [256] Matteo Gigante v Luca Nardi [154] | 4-6,7-6,6-4 | |
| Challenger Milan | 07/06 10:15 | 26 | [256] Matteo Gigante v Giovanni Oradini [437] | 6-1,6-2 | |
| Challenger Milan | 07/04 12:40 | 25 | [148] Francesco Passaro v Matteo Gigante [256] | 5-7,4-6 | |
| Wimbledon | 06/29 10:30 | 19 | [180] Harold Mayot v Matteo Gigante [254] | 6-4,6-2,6-2 | |
| Wimbledon | 06/28 10:00 | 15 | [254] Matteo Gigante v Gabriel Diallo [140] | 6-4,6-4 | |
| Wimbledon | 06/26 10:00 | 14 | Matteo Gigante v Harry Wendelken | 6-3,7-6 | |
| Challenger Parma | 06/21 08:30 | 26 | [242] Matteo Gigante v Stefano Travaglia [256] | 4-6,6-7 | |
| Challenger Parma | 06/19 15:00 | 25 | [150] Jozef Kovalik v Matteo Gigante [242] | 4-6,6-7 | |
| Challenger Perugia | 06/15 10:00 | 26 | [251] Matteo Gigante v Nerman Fatic [271] | 6-4,6-7,3-6 |