Round: 44 Ground: Clay
| ITF Netherlands F4 | 2016/07/02 08:00 | de Bruijn, Ricky v Willekes Macdonald, Robert | 2-6,0-6 |
| ITF Netherlands F2 Qual | 2016/06/18 08:00 | ヤニック・ハンフマン v de Bruijn, Ricky | 7-5,6-0 |
| ITF Netherlands F1 Qual | 2016/06/11 08:00 | Bonapart, Casper v de Bruijn, Ricky | 6-4,6-2 |
| ITF Turkey F11 | 2016/03/13 08:00 | ゴルケ,デルフ v de Bruijn, Ricky | 6-1,6-1 |
| Turkey F10, Singles Qualifying | 2016/03/06 09:00 | de Bruijn, Ricky v Labna, Ramy | 1-6,3-6 |
| Turkey F6, Singles Qualifying | 2016/02/07 09:00 | de Bruijn, Ricky v レチェヴレテル・ルイス | 1-6,3-6 |
| ITF Netherlands F2 Qual | 2015/06/21 09:15 | de Bruijn, Ricky v ブレイク・エリス | 1-6,3-6 |
| ITF Netherlands F2 Qual | 2015/06/20 08:00 | de Bruijn, Ricky v マルセル・マーロン・シュズム | 6-1,6-0 |
| ITF Belgium F4 Qual | 2016/07/02 09:00 | Vanhauwe, Robin v Bant, Jarryd | 4-6,3-6 |
| ITF Belgium F3 Qual | 2016/06/25 09:00 | Vanhauwe, Robin v Seurin, Julien | 3-6,5-7 |
| ITF Belgium F10 Qual | 2015/08/09 09:00 | ロフォ・ラミアラマナナ v Vanhauwe, Robin | 6-0,7-5 |
| ITF Belgium F10 Qual | 2015/08/08 09:00 | Vanhauwe, Robin v Manekas, Athanassios | 7-5,6-4 |