| French Open - Kvinner | 05/21 12:05 | 44 | [119] Natalia Vikhlyantseva v Yanina Wickmayer [154] | 6-3,6-0 | |
| ITF W60 La Bisbal | 05/16 08:30 | 26 | [99] Mandy Minella v Yanina Wickmayer [153] | 6-3,7-6 | |
| ITF W60 La Bisbal | 05/15 12:15 | 25 | [195] Katarina Zavatska v Yanina Wickmayer [153] | 7-5,0-6,2-6 | |
| ITF W80 Cagnes-Sur-Mer | 05/07 12:00 | 25 | [153] Yanina Wickmayer v Ylena In-Albon [182] | 3-6,2-6 | |
| ITF W60 Wiesbaden | 05/02 10:00 | 26 | [255] Cagla Buyukakcay v Yanina Wickmayer [147] | 6-1,3-6,7-6 | |
| ITF W60 Wiesbaden | 05/01 16:00 | 25 | [366] Stephanie Wagner v Yanina Wickmayer [147] | Retired | |
| 2019 Fed Cup | 04/21 13:05 | - | [127] Yanina Wickmayer v Carla Suarez Navarro [27] | 2-6,1-6 | |
| WTA Miami | 03/22 16:00 | 24 | [1] Naomi Osaka v Yanina Wickmayer [141] | 6-0,6-7,6-1 | |
| WTA Miami | 03/21 15:00 | 23 | [142] Sachia Vickery v Yanina Wickmayer [141] | 6-3,3-6,1-6 | |
| WTA Miami | 03/20 15:55 | 45 | [94] Kristyna Pliskova v Yanina Wickmayer [141] | 3-6,3-6 | |
| WTA Miami | 03/18 22:15 | 44 | [141] Yanina Wickmayer v Veronika Kudermetova [81] | 6-4,6-2 | |
| WTA Guadalajara | 03/14 03:05 | 26 | [133] Yanina Wickmayer v Kristyna Pliskova [90] | 6-4,4-6,6-7 | |
| WTA Guadalajara | 03/11 21:00 | 25 | [106] Ana Bogdan v Yanina Wickmayer [133] | 1-6,3-6 | |
| WTA Indian Wells | 03/06 00:40 | 45 | [133] Yanina Wickmayer v Misaki Doi [121] | 6-7,5-7 | |
| WTA Indian Wells | 03/05 01:10 | 44 | [99] Mandy Minella v Yanina Wickmayer [133] | 2-6,3-6 | |
| WTA Indian Wells | 02/27 18:00 | 25 | [127] Yanina Wickmayer v Alison Riske [47] | 6-3,3-6,3-6 | |
| WTA Indian Wells | 02/25 20:35 | 24 | [111] Fiona Ferro v Yanina Wickmayer [127] | 6-1,3-6,3-6 | |
| ITF W60 Shrewsbury | 02/16 13:30 | 29 | [126] Yanina Wickmayer v Vitalia Diatchenko [127] | 7-5,1-6,4-6 | |
| ITF W60 Shrewsbury | 02/15 12:30 | 28 | [126] Yanina Wickmayer v Harmony Tan [301] | 7-5,6-4 | |
| ITF W60 Shrewsbury | 02/14 13:45 | 27 | [126] Yanina Wickmayer v Maia Lumsden [344] | 6-3,6-3 | |
| ITF W60 Shrewsbury | 02/13 10:00 | 26 | [126] Yanina Wickmayer v Jessika Ponchet [234] | 6-2,6-3 | |
| ITF W60 Shrewsbury | 02/12 10:00 | 25 | [126] Yanina Wickmayer v Lesley Kerkhove [220] | 6-2,6-1 | |
| ITF W100 Midland | 02/01 17:00 | 27 | [136] Yanina Wickmayer v Robin Anderson [283] | 3-6,4-6 | |
| ITF W100 Midland | 01/31 19:00 | 26 | [136] Yanina Wickmayer v Ann Li [295] | 4-6,6-3,6-2 | |
| ITF W100 Midland | 01/30 15:00 | 25 | [136] Yanina Wickmayer v Jia-Jing Lu [195] | 6-3,7-5 | |
| WTA Newport Beach | 01/23 18:00 | 25 | [126] Yanina Wickmayer v Allie Kiick [157] | 2-6,2-6 | |
| Australian Open - Kvinner | 01/07 23:00 | 44 | [180] Kaja Juvan v Yanina Wickmayer [126] | 4-6,6-4,7-5 | |
| WTA Brisbane | 12/28 04:00 | 45 | [122] Yanina Wickmayer v Zoe Hives [223] | 6-4,3-6,2-6 | |
| US Open - Kvinner | 08/28 15:00 | 23 | [5] Petra Kvitova v Yanina Wickmayer [94] | 6-1,6-4 | |
| ITF Women Vancouver | 08/16 18:55 | 26 | [287] Rebecca Marino v Yanina Wickmayer [96] | 7-5,7-5 |