| Challenger - Toyota | 11/17 02:30 | 27 | [309] Andrew Whittington v Calvin Hemery [169] | 6-3,3-6,5-7 | |
| Challenger - Toyota | 11/15 04:00 | 26 | [392] Shintaro Imai v Andrew Whittington [309] | 3-6,3-6 | |
| Challenger - Toyota | 11/13 03:55 | 25 | [311] Andrew Whittington v Hiroki Moriya [328] | 6-3,6-4 | |
| Challenger - Camberra 2 | 10/31 01:55 | 25 | [270] Maverick Banes v Andrew Whittington [312] | 6-7,6-3,6-2 | |
| Challenger - Traralgon | 10/26 01:55 | 26 | Andrew Whittington v Jason Kubler | 2-6,2-6 | |
| Challenger - Traralgon | 10/24 02:05 | 25 | Andrew Whittington v Matthew Dellavedova | 6-0,6-3 | |
| ITF - Austrália F7 | 10/12 00:00 | 26 | [319] Andrew Whittington v Nathan Pasha [363] | 7-6,2-6,3-6 | |
| ITF - Austrália F7 | 10/11 00:00 | 25 | Andrew Whittington v Jesse Delaney | 6-3,6-2 | |
| ATP - Montreal - Qualificação | 08/05 21:20 | 45 | [252] Andrew Whittington v Nicolas Mahut [111] | 5-7,6-7 | |
| Challenger - Lexington | 08/01 19:15 | 25 | [199] Cameron Norrie v Andrew Whittington [252] | 4-6,7-6,6-2 | |
| Challenger - Binghamton | 07/25 15:40 | 25 | [336] Dominik Koepfer v Andrew Whittington [228] | 6-4,5-7,6-2 | |
| ATP - Newport - Qualificação | 07/17 16:35 | 46 | [197] Andrew Whittington v Frank Dancevic [422] | 6-3,3-6,6-7 | |
| ATP - Newport - Qualificação | 07/16 18:05 | 45 | [211] Andrew Whittington v Evan King [361] | 7-5,6-0 | |
| Challenger - Winnetka | 07/11 18:40 | 25 | Andrew Whittington v JC Aragone | 5-7,6-3,3-6 | |
| Wimbledon | 07/03 10:30 | 23 | [100] Thiago Monteiro v Andrew Whittington [210] | 4-6,6-3,7-6,7-6 | |
| Wimbledon - Qualificação | 06/29 13:55 | - | [189] Denis Kudla v Andrew Whittington [209] | 6-4,6-2,6-7,6-7,0-6 | |
| Wimbledon - Qualificação | 06/28 15:40 | 45 | [193] Tim Smyczek v Andrew Whittington [209] | 7-6,4-6,4-6 | |
| Wimbledon - Qualificação | 06/26 11:50 | 44 | [209] Andrew Whittington v Stephane Robert [146] | 3-6,7-5,6-4 | |
| Challenger - Ilkley - Qualificação | 06/17 10:00 | 45 | [275] Matthew Ebden v Andrew Whittington [182] | 4-6,6-1,7-6 | |
| Challenger - Nottingham | 06/12 11:25 | 25 | [175] Marc Polmans v Andrew Whittington [182] | 6-4,6-4 | |
| Challenger - Surbiton | 06/08 16:15 | 26 | [180] Andrew Whittington v Reilly Opelka [151] | 3-6,7-6,3-6 | |
| Challenger - Surbiton | 06/08 10:45 | 25 | [180] Andrew Whittington v Taylor Fritz [133] | 7-6,4-6,7-5 | |
| Challenger - Surbiton - Qualificação | 06/05 10:00 | 54 | [236] Roberto Quiroz v Andrew Whittington [180] | 6-7,6-3,6-4 | |
| Challenger - Surbiton - Qualificação | 06/04 15:15 | 46 | [189] Marc Polmans v Andrew Whittington [180] | 6-7,4-6 | |
| Challenger - Surbiton - Qualificação | 06/04 11:50 | 45 | [170] Luke Bambridge v Andrew Whittington [180] | 4-6,6-7 | |
| Open de França - Qualificação | 05/22 11:40 | 44 | [178] Andrew Whittington v Pedro Sousa [155] | 4-6,1-6 | |
| Challenger - Anning | 04/27 03:15 | 26 | [177] Andrew Whittington v Di Wu [233] | 6-2,4-6,2-6 | |
| Challenger - Anning | 04/25 09:30 | 25 | [177] Andrew Whittington v Kimmer Coppejans [171] | 6-3,2-6,7-5 | |
| Challenger - Qingdao | 04/18 02:00 | 25 | [176] Andrew Whittington v Quentin Halys [143] | 0-6,0-6 | |
| ATP - Miami - Qualificação | 03/20 19:30 | 44 | [104] Nicolas Kicker v Andrew Whittington [160] | 7-6,7-6 |