| Challenger Drummondville | 11/12 18:20 | 25 |
[85] Cleeve Harper v
Michael Mmoh
[290] 
|
3-6,3-6 | |
| Challenger Sioux Falls | 10/19 15:00 | 14 |
Cleeve Harper v
Adhithya Ganesan
|
3-6,7-6,4-6 | |
| Challenger Olbia | 10/12 08:00 | 14 | [84] Cleeve Harper v Arthur Reymond [209] | 2-6,1-6 | |
| Davis Cup | 09/13 18:40 | 4 | Cleeve Harper v Orel Kimhi | 6-3,7-6 | |
| Challenger Cancun | 08/14 15:30 | 25 |
[152] Stan Wawrinka
v
Cleeve Harper [90] |
6-3,6-4 | |
| Challenger Cancun | 08/12 22:00 | 19 |
[90] Cleeve Harper v
Manuel Guinard
[498] 
|
Retired | |
| Challenger Cancun | 08/11 23:15 | 14 |
[350] Naoki Nakagawa
v
Cleeve Harper [90] |
3-6,2-6 | |
| Challenger Merida | 03/16 17:00 | 14 | [110] Cleeve Harper v Joshua Sheehy [239] | 4-6,4-6 | |
| Challenger Tenerife Qual | 02/09 15:40 | 14 |
[131] Cleeve Harper v
Ryan Peniston
[439] 
|
5-7,0-6 | |
| Challenger Oeiras | 01/21 10:00 | 19 |
[235] Mark Lajal
v
Cleeve Harper [154] |
6-4,6-2 | |
| Challenger Oeiras | 01/20 11:00 | 14 |
[154] Cleeve Harper v
Aidan Mayo
[274] 
|
5-7,6-1,6-4 | |
| Challenger Oeiras | 01/06 12:50 | 19 |
[314] Ivan Gakhov
v
Cleeve Harper [157] |
6-1,4-6,6-4 | |
| Challenger Oeiras | 01/05 15:50 | 14 |
[468] Sascha Gueymard Wayenburg
v
Cleeve Harper [159] |
7-5,4-6,1-6 | |
| ITF M25 Austin | 11/21 15:50 | 26 |
Cleeve Harper v
Stefan Dostanic
|
2-6,3-6 | |
| ITF M25 Austin | 11/20 17:30 | 25 | Cleeve Harper v Adam Jones | 7-5,6-1 | |
| Challenger Drummondville | 11/10 15:00 | 14 | Antoine Ghibaudo v Cleeve Harper | 6-4,6-4 | |
| Challenger Calgary | 10/15 16:00 | 25 |
[272] Cleeve Harper v
Aidan Mayo
[334]
|
4-6,6-7 | |
| ITF M25 Edmonton | 10/12 16:00 | 26 | Adam Faragcao v Cleeve Harper | 6-4,2-6,1-6 | |
| ITF M25 Edmonton | 10/11 17:00 | 27 | Patrick Maloney v Cleeve Harper | 6-2,6-4 | |
| ITF M25 Edmonton | 10/09 15:55 | 26 | Adam Faragcao v Cleeve Harper | 6-4,2-6,1-6 | |
| ITF M25 Edmonton | 10/08 17:35 | 25 | [287] Cleeve Harper v Louis Wessels [339] | 6-2,6-3 | |
| ITF M25 Sabadell | 09/23 10:00 | 62 | Cleeve Harper v Samuel Brosset | 4-6,6-4,6-10 | |
| ITF M25 Oviedo | 08/27 08:00 | 25 |
[421] Cleeve Harper v
Alex M Pujolras
[383] 
|
1-6,1-6 | |
| ITF M25 Oviedo | 08/26 07:55 | 54 | Cleeve Harper v Ivan Lopez Martos | 6-1,6-2 | |
| ITF M25 Oviedo | 08/25 08:00 | 54 | Cleeve Harper v Samuel D F Garcia | 6-3,6-4 | |
| ITF M25 Santander | 08/20 13:00 | 25 | Cleeve Harper v Inaki Montes-De La Torre | 2-6,1-6 | |
| ITF M25 Santander | 08/19 11:15 | 54 | Cleeve Harper v Valentin Lapalu | 6-3,6-0 | |
| ITF M25 Santander | 08/18 15:30 | 54 | Cleeve Harper v Asier Meneses Perny | 6-2,6-3 | |
| ITF M25 Champaign | 07/24 14:50 | 25 | [495] Harrison Adams v Cleeve Harper [500] | 6-3,6-1 | |
| ITF M25 Champaign | 07/23 14:45 | 54 | Alexander Kotzen v Cleeve Harper | 0-6,6-7 |
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