Stadium: Court 11 Round: 14 Ground: Clay
| Challenger Nanchang | 2018/04/18 03:00 | Cem Ilkel v Prajnesh Gunneswaran | 4-6,4-6 |
| Challenger Iasi | 2020/09/15 08:45 | Cem Ilkel v Malek Jaziri | 2-6,4-6 |
| Davis Cup | 2020/03/07 09:50 | Cem Ilkel v Edan Leshem | 2-6,6-7 |
| Davis Cup | 2020/03/06 08:55 | Cem Ilkel v Daniel Cukierman | 6-7,2-6 |
| ITF M25 Antalya | 2020/02/26 08:45 | Cem Ilkel v Duje Ajdukovic | 4-6,6-4,6-7 |
| Challenger Bergamo | 2020/02/21 10:00 | Hugo Gaston v Cem Ilkel | 6-4,6-4 |
| Challenger Bergamo | 2020/02/20 12:05 | Raul Brancaccio v Cem Ilkel | 1-6,6-7 |
| Challenger Bergamo | 2020/02/18 11:45 | Viktor Durasovic v Cem Ilkel | 3-6,4-6 |
| Challenger Cherbourg | 2020/02/11 13:20 | Cem Ilkel v Mirza Basic | 6-3,2-6,3-6 |
| ATP Kitzbuhel | 2020/09/08 10:00 | Marc-Andrea Huesler v Prajnesh Gunneswaran | 6-3,6-3 |
| ATP Kitzbuhel | 2020/09/07 12:50 | Sandro Kopp v Prajnesh Gunneswaran | 4-6,6-1,4-6 |
| Davis Cup | 2020/03/06 14:00 | Borna Gojo v Prajnesh Gunneswaran | 3-6,6-4,6-2 |
| ATP Dubai | 2020/02/25 10:00 | Prajnesh Gunneswaran v Dennis Novak | 4-6,3-6 |
| Challenger Bengaluru | 2020/02/13 10:55 | Prajnesh Gunneswaran v Benjamin Bonzi | 6-7,0-6 |
| Challenger Bengaluru | 2020/02/12 05:30 | Prajnesh Gunneswaran v Sebastian Fanselow | 6-2,4-6,6-4 |
| ATP Pune | 2020/02/06 13:10 | Soonwoo Kwon v Prajnesh Gunneswaran | 6-3,7-6 |
| ATP Pune | 2020/02/04 13:10 | Prajnesh Gunneswaran v Yannick Maden | 7-6,7-6 |