| Challenger Oeiras | 01/02 14:20 | 25 | [250] Matteo Gigante v Clement Tabur [321] | 6-3,7-5 | |
| Challenger Ortisei | 10/24 17:10 | 25 | [237] Matteo Gigante v Borna Gojo [182] | 2-6,4-6 | |
| Challenger Genova | 09/21 09:30 | 26 | [197] Sebastian Ofner v Matteo Gigante [241] | 2-6,6-1,6-3 | |
| Challenger Genova | 09/20 08:00 | 25 | [241] Matteo Gigante v Alexey Vatutin [271] | 6-1,1-6,6-1 | |
| Challenger Genova | 09/19 10:30 | 19 | Matteo Gigante v Stefano Napolitano | 6-2,1-6,7-6 | |
| Challenger Genova | 09/18 08:00 | 14 | Matteo Gigante v Lorenzo Bocchi | 6-3,6-3 | |
| Challenger Como | 09/02 15:35 | 27 | [264] Matteo Gigante v Francesco Passaro [146] | 7-6,1-6,5-7 | |
| Challenger Como | 09/01 08:00 | 26 | [244] Miljan Zekic v Matteo Gigante [264] | 3-6,6-3,6-7 | |
| Challenger Como | 08/29 14:35 | 25 | [264] Matteo Gigante v Gian Marco Moroni [238] | 6-7,6-2,6-1 | |
| Challenger Prague | 08/26 08:00 | 27 | [269] Matteo Gigante v Lucas Gerch [384] | 5-7,2-6 | |
| Challenger Prague | 08/24 08:00 | 26 | [269] Matteo Gigante v Michael Vrbensky [399] | 6-2,6-3 | |
| Challenger Prague | 08/23 11:30 | 25 | [269] Matteo Gigante v Roman A Burruchaga [311] | 7-6,2-6,6-2 | |
| Challenger San Marino | 08/10 17:10 | 26 | [248] Fabian Marozsan v Matteo Gigante [274] | 6-2,6-2 | |
| Challenger San Marino | 08/09 10:00 | 25 | [244] Jelle Sels v Matteo Gigante [274] | 2-6,3-6 | |
| Challenger San Benedetto | 07/26 15:30 | 25 | Matteo Gigante v Luciano Darderi | Cancelled | |
| Challenger Trieste | 07/19 08:00 | 25 | [275] Matteo Gigante v Lukas Neumayer [345] | 6-1,3-6,4-6 | |
| Challenger Verona | 07/13 19:00 | 26 | [296] Matteo Gigante v Norbert Gombos [112] | 6-7,4-6 | |
| Challenger Verona | 07/12 11:00 | 25 | [296] Matteo Gigante v Luca Nardi [174] | 6-4,3-6,7-6 | |
| Challenger Verona | 07/11 11:25 | 19 | [296] Matteo Gigante v Francesco Forti [487] | 6-2,6-2 | |
| Challenger Verona | 07/10 12:15 | 14 | [307] Matteo Gigante v Giovanni Oradini [468] | 6-4,6-3 | |
| Challenger Todi | 07/08 09:00 | 26 | [120] Pedro Cachin v Matteo Gigante [307] | 7-6,6-0 | |
| Challenger Todi | 07/05 19:50 | 25 | [307] Matteo Gigante v Federico Gaio [211] | 6-3,7-5 | |
| Challenger Milan | 06/24 12:30 | 27 | [322] Matteo Gigante v Fabian Marozsan [297] | 6-7,2-6 | |
| Challenger Milan | 06/23 13:00 | 26 | [171] Marco Cecchinato v Matteo Gigante [322] | 6-7,1-6 | |
| Challenger Milan | 06/20 15:00 | 25 | [322] Matteo Gigante v Francesco Maestrelli [379] | 6-4,6-2 | |
| Challenger Perugia | 06/07 11:55 | 25 | [333] Matteo Gigante v Cristian Rodriguez [440] | 3-6,2-6 | |
| Challenger Forli | 06/04 17:00 | 28 | Lorenzo Musetti v Matteo Gigante | 3-6,6-1,6-1 | |
| Challenger Forli | 06/03 15:30 | 27 | Tomas Martin Etcheverry v Matteo Gigante | 2-6,3-6 | |
| Challenger Forli | 06/02 09:00 | 26 | Thomas Fabbiano v Matteo Gigante | 6-7,4-6 | |
| Challenger Forli | 05/31 12:00 | 25 | Matteo Gigante v Gianluca Mager | 6-3,3-6,6-3 |