Round: 54 Ground: Hardcourt outdoor
| ITF Tunisia F9 | 2016/03/07 08:30 | Gray, Jonathan v Malyshev, Maksim | 6-4,6-4 |
| ITF China F7 Qual | 2016/05/16 03:35 | Malyshev, Maksim v Wei-De Lin | 4-6,3-6 |
| ITF China F7 Qual | 2016/05/15 07:30 | Jake Delaney v Malyshev, Maksim | 4-6,0-6 |
| ITF China F6 Qual | 2016/05/07 03:30 | Lo, Chien Hsun v Malyshev, Maksim | 5-7,7-6,6-0 |
| ITF Tunisia F11 | 2016/03/22 08:30 | Malyshev, Maksim v Joris De Loore | 0-6,2-6 |
| ITF Tunisia F11 Qual | 2016/03/21 08:30 | Dijkhuizen, Marc v Malyshev, Maksim | 6-7,3-6 |
| ITF Tunisia F11 Qual | 2016/03/20 08:30 | Nematzadeh, Keyvan v Malyshev, Maksim | 6-3,6-7,4-6 |
| Tunisia F10, Singles Qualifying | 2016/03/14 08:30 | Tinelli, Matteo v Malyshev, Maksim | 6-4,6-3 |
| Tunisia F10, Singles Qualifying | 2016/03/13 09:30 | Sikman, Philip v Malyshev, Maksim | 0-6,3-6 |
| Tunisia F10, Singles Qualifying | 2016/03/15 08:30 | Crepatte, Baptiste v Gray, Jonathan | 6-3,6-3 |
| ITF Tunisia F9 | 2016/03/10 11:50 | Gray, Jonathan v Zhurbin, Alexander | 7-6,1-6,4-6 |
| ITF Tunisia F9 | 2016/03/09 09:45 | Saavedra-Corvalan, Cristobal v Gray, Jonathan | 4-6,3-6 |
| ITF Tunisia F9 | 2016/03/07 08:30 | Gray, Jonathan v Malyshev, Maksim | 6-4,6-4 |
| ITF Great Britain F3 Qual | 2016/02/14 13:00 | Marsalek, James v Gray, Jonathan | 6-1,4-6,6-4 |
| ITF Great Britain F3 Qual | 2016/02/14 09:30 | Bjerke, Joachim v Gray, Jonathan | 4-6,3-6 |
| Tunisia F4, Singles Qualifying | 2016/02/03 08:30 | Gray, Jonathan v Kim, Cheong-Eui | 2-6,2-6 |
| Tunisia F3, Singles Qualifying | 2016/01/25 13:00 | Gray, Jonathan v Romero de Avila Senise, Alberto | 6-3,5-7,1-6 |