| Challenger Perugia | 06/12 16:00 | 25 | [251] Matteo Gigante v Alessandro Giannessi [238] | Retired | |
| Challenger Vicenza | 05/30 13:10 | 25 | [204] Matteo Gigante v Santiago Rodriguez Taverna [245] | 6-1,1-6,1-6 | |
| French Open | 05/24 08:00 | 15 | [124] Facundo Bagnis v Matteo Gigante [204] | 1-6,6-3,6-2 | |
| French Open | 05/22 08:00 | 14 | [184] Seong-Chen Hong v Matteo Gigante [204] | 5-7,4-6 | |
| Challenger Tunis | 05/16 09:50 | 25 | [202] Matteo Gigante v Tomas Barrios Vera [143] | Retired | |
| ATP Rome | 05/08 12:05 | 14 | [104] Thanasi Kokkinakis v Matteo Gigante [202] | 7-5,6-3 | |
| ATP Barcelona | 04/15 10:55 | 14 | [103] Pavel Kotov v Matteo Gigante [196] | 3-6,7-6,6-4 | |
| Challenger Barletta | 04/06 09:55 | 26 | [168] Franco Agamenone v Matteo Gigante [192] | Retired | |
| Challenger Barletta | 04/03 12:25 | 25 | [220] Miljan Zekic v Matteo Gigante [192] | 6-3,1-6,6-7 | |
| Challenger Sanremo | 03/27 13:55 | 25 | [184] Andrea Pellegrino v Matteo Gigante [199] | 7-6,6-4 | |
| Challenger Zadar | 03/24 10:00 | 27 | [137] Sebastian Ofner v Matteo Gigante [199] | 6-4,6-1 | |
| Challenger Zadar | 03/23 10:00 | 26 | [199] Matteo Gigante v Hamad Medjedovic [192] | 6-1,6-2 | |
| Challenger Zadar | 03/21 13:55 | 25 | [394] Julian Ocleppo v Matteo Gigante [199] | 3-6,6-2,4-6 | |
| Challenger Lugano | 03/06 18:20 | 25 | [170] Otto Virtanen v Matteo Gigante [196] | 6-7,6-3,6-2 | |
| Challenger Rovereto | 02/20 16:55 | 25 | [193] Matteo Gigante v Marcello Serafini [369] | 4-6,6-2,4-6 | |
| Challenger Tenerife | 02/12 12:00 | 29 | [232] Matteo Gigante v Stefano Travaglia [409] | 6-3,6-2 | |
| Challenger Tenerife | 02/11 15:40 | 28 | [232] Matteo Gigante v Riccardo Bonadio [187] | 5-7,7-6,6-3 | |
| Challenger Tenerife | 02/10 15:55 | 27 | [232] Matteo Gigante v Pablo Llamas Ruiz [352] | 6-2,6-4 | |
| Challenger Tenerife | 02/08 15:15 | 26 | [109] Francesco Passaro v Matteo Gigante [232] | 7-5,2-6,2-6 | |
| Challenger Tenerife | 02/07 12:40 | 25 | [232] Matteo Gigante v Daniel Rincon [316] | 6-4,6-2 | |
| Challenger Tenerife Qual | 02/06 13:05 | 19 | [232] Matteo Gigante v Giovanni Fonio [364] | 4-6,4-6 | |
| Challenger Tenerife Qual | 02/06 10:00 | 14 | [232] Matteo Gigante v Mark Whitehouse [265] | 6-1,6-3 | |
| Challenger Tenerife | 01/31 10:00 | 25 | [235] Matteo Gigante v Shintaro Mochizuki [311] | 4-6,6-2,1-6 | |
| Challenger Tenerife | 01/30 10:00 | 19 | [235] Matteo Gigante v Stefano Travaglia [323] | 6-3,6-1 | |
| Challenger Tenerife | 01/29 12:40 | 14 | Matteo Gigante v Miguel Garcia | 6-2,6-1 | |
| Challenger Tenerife | 01/20 17:05 | 27 | [258] Matteo Gigante v Francesco Maestrelli [197] | 6-1,1-6,3-6 | |
| Challenger Tenerife | 01/19 17:00 | 26 | [218] Nicolas Moreno De Alboran v Matteo Gigante [258] | 6-7,5-7 | |
| Challenger Tenerife | 01/17 14:40 | 25 | [322] Ulises Blanch v Matteo Gigante [258] | 2-6,3-6 | |
| Challenger Oeiras | 01/09 15:45 | 25 | [304] Pierre-Hugues Herbert v Matteo Gigante [250] | 3-6,6-4,6-4 | |
| Challenger Oeiras | 01/05 11:00 | 26 | [250] Matteo Gigante v Dino Prizmic [475] | 6-2,1-6,3-6 |