| Challenger Canberra | 01/06 03:20 | 24 | [122] Prajnesh Gunneswaran v Jason Kubler [257] | 7-5,6-3 | |
| Challenger Pune | 11/14 10:30 | 26 | [95] Prajnesh Gunneswaran v Tim Van Rijthoven [324] | 6-4,5-7,3-6 | |
| Challenger Pune | 11/13 10:50 | 25 | Prajnesh Gunneswaran v Chandril Sood | 6-1,6-3 | |
| Challenger Liuzhou | 10/24 02:00 | 26 | [90] Prajnesh Gunneswaran v Tung-Lin Wu [239] | Walkover | |
| Challenger Liuzhou | 10/22 06:15 | 25 | [90] Prajnesh Gunneswaran v Nicolas Barrientos [348] | 6-2,6-1 | |
| Challenger Ningbo | 10/18 05:20 | 27 | [82] Prajnesh Gunneswaran v Steven Diez [156] | 3-6,4-6 | |
| Challenger Ningbo | 10/17 07:15 | 26 | [82] Prajnesh Gunneswaran v Tsung-Hua Yang [308] | 7-6,6-3 | |
| Challenger Ningbo | 10/15 06:25 | 25 | [82] Prajnesh Gunneswaran v Max Purcell [227] | 6-3,6-4 | |
| Challenger Kaohsiung | 09/19 05:45 | 26 | [205] Enrique Lopez-Perez v Prajnesh Gunneswaran [82] | 5-7,7-5,6-4 | |
| Challenger Kaohsiung | 09/17 12:15 | 25 | [286] Shuichi Sekiguchi v Prajnesh Gunneswaran [82] | 3-6,2-6 | |
| Challenger Shanghai | 09/14 03:00 | 28 | [85] Prajnesh Gunneswaran v Yasutaka Uchiyama [165] | 6-7,4-6 | |
| Challenger Shanghai | 09/13 03:00 | 27 | [85] Prajnesh Gunneswaran v Hiroki Moriya [232] | 6-4,6-4 | |
| Challenger Shanghai | 09/12 05:20 | 26 | [85] Prajnesh Gunneswaran v Goncalo Oliveira [254] | 6-3,6-4 | |
| Challenger Shanghai | 09/10 05:50 | 25 | [85] Prajnesh Gunneswaran v James Ward [291] | 6-4,7-6 | |
| Challenger Jinan | 09/06 06:55 | 27 | [88] Prajnesh Gunneswaran v Go Soeda [155] | 6-7,6-3,3-6 | |
| Challenger Jinan | 09/05 07:05 | 26 | [88] Prajnesh Gunneswaran v Tung-Lin Wu [269] | 6-4,7-6 | |
| Challenger Jinan | 09/04 06:00 | 25 | [88] Prajnesh Gunneswaran v Renta Tokuda [471] | 6-2,6-2 | |
| US Open | 08/26 17:05 | 23 | [88] Prajnesh Gunneswaran v Daniil Medvedev [5] | 4-6,1-6,2-6 | |
| ATP Winston-Salem | 08/20 18:25 | 25 | [30] Benoit Paire v Prajnesh Gunneswaran [89] | 6-3,7-5 | |
| ATP Winston-Salem | 08/18 21:15 | 24 | [91] Prajnesh Gunneswaran v Cedrik-Marcel Stebe [253] | 6-3,6-4 | |
| ATP Los Cabos | 08/01 01:50 | 26 | [90] Prajnesh Gunneswaran v Taylor Fritz [28] | 6-4,3-6,2-6 | |
| ATP Los Cabos | 07/30 00:00 | 25 | [90] Prajnesh Gunneswaran v John Millman [67] | 6-4,1-6,6-2 | |
| ATP Atlanta | 07/23 16:30 | 25 | [117] Soon Woo Kwon v Prajnesh Gunneswaran [88] | 6-7,7-5,6-0 | |
| ATP Newport | 07/15 17:25 | 25 | [98] Marcel Granollers v Prajnesh Gunneswaran [89] | 6-2,6-2 | |
| Wimbledon | 07/01 15:05 | 23 | [93] Prajnesh Gunneswaran v Milos Raonic [17] | 6-7,4-6,2-6 | |
| ATP Antalya | 06/25 12:30 | 26 | [75] Lorenzo Sonego v Prajnesh Gunneswaran [94] | 6-7,6-0,7-5 | |
| ATP Antalya | 06/24 10:30 | 25 | [94] Prajnesh Gunneswaran v Janko Tipsarevic [286] | 6-0,7-6 | |
| ATP Queens | 06/15 11:40 | 64 | [204] James Ward v Prajnesh Gunneswaran [91] | 6-1,6-4 | |
| ATP Stuttgart | 06/08 10:40 | 64 | [88] Prajnesh Gunneswaran v Matteo Viola [250] | Retired | |
| French Open | 05/26 13:10 | 23 | [86] Prajnesh Gunneswaran v Hugo Dellien [92] | 1-6,3-6,1-6 |
Prajnesh Gunneswaran (ur. 12 listopada 1989 w Ćennaju) – indyjski tenisista.