| ITF M15 Cancun | 03/11 20:40 | 25 | Peter Bertran v Jacob Grills | 7-5,4-6,1-6 | |
| ITF M25 Las Vegas | 03/05 20:50 | 26 | [415] Justin Butsch v Jacob Grills [463] | 7-5,7-5 | |
| ITF M25 Las Vegas | 03/04 17:55 | 25 | Mousheg Hovhannisyan v Jacob Grills | 2-6,1-6 | |
| Challenger Calgary | 02/24 20:55 | 24 | [440] Jacob Grills v Patrik Niklas-Salminen [430] | 2-6,4-6 | |
| Challenger Launceston | 02/04 03:20 | 25 | [449] Jacob Grills v Tung-Lin Wu [223] | 6-4,4-6,6-7 | |
| Challenger Launceston | 02/03 02:30 | 24 | Matthew C Romios v Jacob Grills | 1-6,0-6 | |
| Challenger Burnie | 01/28 01:05 | 25 | [445] Jacob Grills v Zhe Li [206] | 1-6,0-6 | |
| Challenger Burnie | 01/27 01:15 | 24 | [359] Dayne Kelly v Jacob Grills [445] | 2-6,7-6,4-6 | |
| Challenger Bendigo | 01/12 02:30 | 24 | [446] Jacob Grills v Matias Franco Descotte [381] | 4-6,6-2,4-6 | |
| Australian Open WC | 12/09 02:35 | 26 | [451] Jacob Grills v Aleksandar Vukic [275] | 4-6,4-6,3-6 | |
| Challenger Playford 2 | 10/30 01:00 | 25 | [137] Marc Polmans v Jacob Grills [416] | 6-4,4-6,6-3 | |
| Challenger Playford 2 | 10/28 04:55 | 24 | [416] Jacob Grills v Brandon Walkin [330] | 7-6,6-1 | |
| Challenger Traralgon | 10/21 01:15 | 24 | [418] Dayne Kelly v Jacob Grills [439] | 6-3,5-7,7-6 | |
| ITF M25 Toowoomba | 10/13 03:15 | 29 | Dayne Kelly v Jacob Grills | 1-6,6-3,6-0 | |
| ITF M25 Toowoomba | 10/12 01:30 | 28 | [322] Maverick Banes v Jacob Grills [443] | 2-6,3-6 | |
| ITF M25 Toowoomba | 10/11 00:30 | 27 | [443] Jacob Grills v Harry Bourchier [312] | Retired | |
| ITF M25 Toowoomba | 10/10 00:00 | 26 | Jacob Grills v Will Maher | 7-5,6-1 | |
| ITF M25 Toowoomba | 10/08 04:15 | 25 | Jacob Grills v Ajeet Rai | 2-6,6-1,6-1 | |
| ITF M25 Brisbane | 10/03 00:00 | 26 | [424] Jacob Grills v Thomas Fancutt [320] | 7-6,3-6,5-7 | |
| ITF M25 Brisbane | 10/01 03:50 | 25 | Jacob Grills v Alexander Crnokrak | 0-6,6-3,6-1 | |
| Challenger Kaohsiung | 09/16 02:45 | 24 | [369] Jacob Grills v Evan King [348] | 4-6,6-3,2-6 | |
| Challenger Shanghai | 09/09 06:05 | 24 | [372] Jacob Grills v Shuichi Sekiguchi [304] | 6-3,1-6,1-6 | |
| Challenger Jinan | 09/03 02:00 | 24 | [352] Teymuraz Gabashvili v Jacob Grills [372] | 6-4,5-7,6-1 | |
| Challenger Baotou | 08/26 02:00 | 24 | [372] Jacob Grills v Di Wu [476] | 6-7,4-6 | |
| ATP Los Cabos | 07/29 00:00 | 164 | [121] Dominik Koepfer v Jacob Grills [387] | 6-3,7-6 | |
| ATP Los Cabos | 07/28 01:25 | 64 | [387] Jacob Grills v Lukas Lacko [214] | 6-3,6-2 | |
| Challenger Granby | 07/22 17:30 | 24 | [249] Cem Ilkel v Jacob Grills [387] | 6-1,6-0 | |
| Challenger Gatineau | 07/16 18:10 | 24 | [223] Yosuke Watanuki v Jacob Grills [370] | 6-7,6-1,6-0 | |
| Challenger Gatineau | 07/15 13:00 | 166 | Jacob Grills v Justin Boulais | Retired | |
| Challenger Winnipeg | 07/10 15:00 | 24 | [369] Jacob Grills v Shintaro Imai [491] | 7-6,6-7,0-6 |