| Challenger Mouilleron le Captif | 10/01 13:00 | 14 | [362] Arthur Fery v Robert Galloway [52] | 6-3,7-5 | |
| Challenger Ostrava | 04/23 12:50 | 14 | Robert Galloway v Karl Friberg | 6-7,4-6 | |
| Challenger Gwangju | 10/03 02:00 | 19 | [457] Naoki Nakagawa v Robert Galloway [89] | 7-6,6-3 | |
| Challenger Gwangju | 10/02 01:00 | 14 | Robert Galloway v Cheong-Eui Kim | 6-3,6-2 | |
| ATP Washington | 07/30 15:05 | 45 | [90] Robert Galloway v Borna Gojo [196] | 3-6,4-6 | |
| Challenger Savannah | 04/24 15:55 | 14 | [421] Andrew Harris v Robert Galloway [103] | 6-3,6-3 | |
| Challenger Knoxville | 11/07 15:00 | 14 | [118] Robert Galloway v Sasikumar Mukund [383] | 2-6,4-6 | |
| Challenger Charlottesville | 10/31 16:00 | 14 | [117] Robert Galloway v Aidan Mchugh [374] | 6-1,3-6,1-6 | |
| Challenger Alicante | 10/11 09:00 | 19 | [116] Robert Galloway v Georgii Kravchenko [452] | 6-4,1-6,2-6 | |
| Challenger Alicante | 10/10 10:25 | 26 | Ivan Nedelko v Robert Galloway | 6-2,2-6,6-7 | |
| Challenger Alicante | 10/10 10:00 | - | Vladyslav Orlov v Robert Galloway | View | |
| Challenger Porto | 06/28 13:00 | 19 | [254] Yosuke Watanuki v Robert Galloway [111] | 6-1,6-1 | |
| Challenger Porto | 06/27 14:10 | 26 | Robert Galloway v Alexander Zhurbin | 6-2,6-2 | |
| Challenger Orlando | 06/06 16:50 | 14 | [123] Robert Galloway v Stefan Kozlov [366] | 4-6,6-7 | |
| ATP Singapore | 02/21 04:00 | 19 | [217] Thai-Son Kwiatkowski v Robert Galloway [123] | 6-2,6-3 | |
| ATP Singapore | 02/20 03:00 | 14 | [123] Robert Galloway v Vladyslav Orlov [351] | 6-4,6-4 | |
| Challenger Poprad Tatry Qual | 06/16 10:05 | 45 | [392] Andreas H-Maurer v Robert Galloway [204] | 6-4,7-5 | |
| Challenger Loughborough Qual | 05/19 13:30 | 45 | Robert Galloway v Jurij Rodionov | 0-6,5-7 | |
| Challenger Lisbon Qual | 05/13 14:35 | 46 | [340] Joris De Loore v Robert Galloway [218] | 6-1,6-1 | |
| Challenger Lisbon Qual | 05/12 14:55 | 45 | [218] Robert Galloway v Hunter Reese [172] | 6-3,6-1 | |
| Challenger Tallahassee Qual | 04/21 14:00 | 45 | [178] Nathaniel Lammons v Robert Galloway [262] | 7-5,6-4 | |
| Challenger Sarasota Qual | 04/14 16:20 | 45 | Robert Galloway v Samuel Shropshire | 2-6,2-6 | |
| ITF Bahrain F1 | 03/22 14:15 | 27 | Robert Galloway v Riccardo Maiga | 4-6,2-6 | |
| ITF Bahrain F1 | 03/21 14:00 | 26 | Robert Galloway v Palaphoom Kova`ted | 6-7,6-1,7-6 | |
| ITF Bahrain F1 | 03/20 16:00 | 25 | [336] Fred Simonsson v Robert Galloway [260] | 7-6,4-6,4-6 | |
| ITF Bahrain F1 Qual | 03/18 12:00 | 54 | Robert Galloway v Rahul Jaideep | 7-6,6-0 | |
| ITF South Africa F3 Qual | 12/03 17:05 | 44 | Jesper De Jong v Robert Galloway | 7-5,6-4 | |
| ITF USA F32 | 09/24 18:00 | 60 | Strong Kirchheimer v Robert Galloway | 6-3,6-4 | |
| ITF USA F31 | 09/16 17:15 | 60 | Julian Cash v Robert Galloway | 6-4,6-4 | |
| ITF USA F30 | 09/10 16:00 | 60 | Tristan Boyer v Robert Galloway | 6-3,4-6,6-4 |