Round: 44 Ground: Grass
| ITF Greece F5 | 2016/04/24 07:00 | O'Mara, Jonny v Glasspool, Lloyd | 3-6,6-4,6-7 |
| ITF Greece F5 | 2016/04/23 07:00 | Glasspool, Lloyd v Lescure, Mick | 6-3,6-3 |
| ITF Greece F5 | 2016/04/22 08:45 | Daniel Cukierman v Glasspool, Lloyd | 4-6,4-6 |
| ITF Greece F5 | 2016/04/21 10:15 | Callahan, Hunter v Glasspool, Lloyd | 6-7,2-6 |
| ITF Greece F5 | 2016/04/20 10:20 | Krainik, Pavel v Glasspool, Lloyd | 3-6,0-6 |
| ITF Greece F4 | 2016/04/17 09:05 | Mertens, Yannick v Glasspool, Lloyd | 6-2,7-5 |
| ITF Greece F4 | 2016/04/16 07:00 | Glasspool, Lloyd v Darian King | 6-3,6-2 |
| ITF Greece F4 | 2016/04/15 07:00 | Glasspool, Lloyd v Brechemier, Thomas | 6-4,6-2 |
| French Open Qual | 2016/05/18 13:20 | Marco Trungelliti v Novikov, Dennis | 7-5,3-6,7-5 |
| French Open Qual | 2016/05/16 10:15 | Noah Rubin v Novikov, Dennis | 3-6,4-6 |
| Challenger - Bordeaux | 2016/05/09 13:15 | Gastao Elias v Novikov, Dennis | 4-6,6-3,6-1 |
| Challenger - Tallahassee | 2016/04/25 18:15 | Lapentti, Giovanni v Novikov, Dennis | 7-6,6-3 |
| Challenger - Savannah | 2016/04/19 15:00 | Henri Laaksonen v Novikov, Dennis | 7-5,6-1 |
| Challenger - Sarasota | 2016/04/14 16:55 | Fratangelo, Bjorn v Novikov, Dennis | 6-4,6-4 |
| Challenger - Sarasota | 2016/04/12 18:40 | Tursunov, Dmitry v Novikov, Dennis | 4-6,4-6 |
| ATP Houston Qual | 2016/04/02 15:00 | Novikov, Dennis v Opelka, Reilly | 4-6,3-6 |