| Challenger - Numeá | 01/10 23:00 | 28 | [219] Matteo Viola v Jeffrey John Wolf [185] | 2-6,2-6 | |
| Challenger - Numeá | 01/10 00:00 | 27 | [177] Roberto Marcora v Matteo Viola [219] | 6-7,6-7 | |
| Challenger - Numeá | 01/09 00:00 | 26 | [170] Yannick Hanfmann v Matteo Viola [219] | 4-6,7-6,4-6 | |
| Challenger - Numeá | 01/08 01:35 | 25 | [219] Matteo Viola v Zdenek Kolar [226] | 6-4,4-6,6-4 | |
| Challenger - Numeá | 01/06 06:05 | 24 | [219] Matteo Viola v Andrea Collarini [190] | 6-3,7-6 | |
| Challenger - Ortisei | 11/11 15:20 | 24 | [227] Matteo Viola v Andrea Pellegrino [353] | 4-6,5-7 | |
| Challenger - Bratislava | 11/04 12:10 | 24 | [190] Roberto Marcora v Matteo Viola [225] | 3-6,6-3,7-6 | |
| Challenger - Brest | 10/23 19:05 | 25 | [230] Matteo Viola v Jiri Vesely [121] | 1-6,2-6 | |
| Challenger - Brest | 10/22 08:00 | 24 | [230] Matteo Viola v Maxime Hamou [367] | 6-4,6-3 | |
| Challenger - Nur-Sultã 2 | 10/02 08:40 | 25 | [378] Illya Marchenko v Matteo Viola [212] | 6-4,6-3 | |
| ATP - São Peterburgo | 09/17 14:05 | 25 | [118] Evgeny Donskoy v Matteo Viola [218] | 6-2,6-1 | |
| ATP - São Peterburgo | 09/16 10:00 | 164 | [135] Ilya Ivashka v Matteo Viola [204] | 6-4,6-2 | |
| ATP - São Peterburgo | 09/15 10:05 | 64 | Alexander Vasilenko v Matteo Viola | 2-6,7-5,2-6 | |
| Challenger - Istambul | 09/12 07:00 | 26 | [480] David Poljak v Matteo Viola [204] | 6-7,6-4,6-4 | |
| Challenger - Istambul | 09/11 10:15 | 25 | [257] Tristan Lamasine v Matteo Viola [204] | 4-6,1-6 | |
| Challenger - Cassis | 09/03 08:00 | 24 | Antoine Escoffier v Matteo Viola | Cancelled | |
| Challenger - Maiorca | 09/01 17:30 | 29 | [209] Emil Ruusuvuori v Matteo Viola [240] | 6-0,6-1 | |
| Challenger - Maiorca | 08/31 15:30 | 28 | [240] Matteo Viola v Daniel Masur [318] | 7-6,4-6,6-2 | |
| Challenger - Maiorca | 08/30 17:55 | 27 | [239] Blaz Kavcic v Matteo Viola [240] | 2-6,1-6 | |
| Challenger - Maiorca | 08/29 17:20 | 26 | [240] Matteo Viola v Andy Murray [328] | 3-6,6-4,7-6 | |
| Challenger - Maiorca | 08/27 14:30 | 25 | [220] Enrique Lopez-Perez v Matteo Viola [240] | 6-7,7-6,0-6 | |
| Challenger - Maiorca | 08/26 15:00 | 24 | [371] Fred Gil v Matteo Viola [240] | 2-6,2-6 | |
| Open dos EUA | 08/20 18:15 | 44 | [238] Matteo Viola v Jannik Sinner [131] | 1-6,0-6 | |
| Challenger - Portoroz | 08/15 18:20 | 26 | [219] Constant Lestienne v Matteo Viola [245] | 6-0,6-1 | |
| Challenger - Portoroz | 08/14 13:30 | 25 | [432] Miljan Zekic v Matteo Viola [245] | 0-6,3-6 | |
| Challenger - Segóvia | 08/01 12:40 | 26 | [287] Pavel Kotov v Matteo Viola [246] | 6-1,6-3 | |
| Challenger - Segóvia | 07/30 09:15 | 25 | [433] Felipe M R Alves v Matteo Viola [246] | 2-6,1-6 | |
| Challenger - Tampere | 07/24 13:00 | 25 | Matteo Viola v Patrik Niklas-Salminen | 6-1,4-6,1-6 | |
| Challenger - Nur-Sultã | 07/19 05:00 | 27 | [247] Matteo Viola v Sebastian Korda [382] | 4-6,5-7 | |
| Challenger - Nur-Sultã | 07/18 05:00 | 26 | [196] Aleksandr Nedovyesov v Matteo Viola [247] | 6-7,4-6 |