Round: 29 Ground: Grass
| Challenger Seville MD | 2019/09/10 17:40 | Djokovic/Gomez-Herrera v Cachin/Zapata Miralles | 3-6,6-3,7-10 |
| Challenger Marbella MD | 2019/03/26 13:55 | Krawietz/Mies v Djokovic/Gomez-Herrera | 6-1,6-3 |
| Challenger Marbella MD | 2018/03/29 15:00 | Djokovic/Gomez-Herrera v Andreozzi/Behar | 6-1,5-7,5-10 |
| Challenger Marbella MD | 2018/03/26 13:30 | Djokovic/Gomez-Herrera v Bolelli/Giannessi | 6-4,6-2 |
| ITF Greece F8 MD | 2017/11/11 13:30 | Berg/Hovhannisyan v Djokovic/Gomez-Herrera | 1-6,2-6 |
| ITF Greece F8 MD | 2017/11/10 13:30 | Djokovic/Gomez-Herrera v Haim/Hirschmueller | 6-2,6-2 |
| ITF Greece F8 MD | 2017/11/09 13:00 | Griekspoor/Seemann v Djokovic/Gomez-Herrera | 5-7,5-7 |
| ITF Greece F8 MD | 2017/11/07 12:25 | Djokovic/Gomez-Herrera v Diaz-Figueroa/Gomez | 6-3,7-6 |
| ATP Estoril MD | 2021/04/28 11:00 | Bolelli/Gonzalez v Klaasen/Mclachlan | 2-6,3-6 |
| ATP Belgrade MD | 2021/04/22 10:00 | Brkic/Cacic v Bolelli/Gonzalez | 0-6,7-6,10-8 |
| ATP Belgrade MD | 2021/04/21 14:45 | Kecmanovic/Lajovic v Bolelli/Gonzalez | 4-6,4-6 |
| ATP Santiago MD | 2021/03/14 16:45 | Bolelli/Gonzalez v Delbonis/Munar | 7-6,6-4 |
| ATP Santiago MD | 2021/03/12 15:00 | Klaasen/Mclachlan v Bolelli/Gonzalez | 4-6,4-6 |
| ATP Santiago MD | 2021/03/11 18:40 | Bolelli/Gonzalez v Arneodo/Paire | 6-2,7-6 |
| ATP Santiago MD | 2021/03/10 20:00 | Bolelli/Gonzalez v Brkic/Cacic | 7-6,6-3 |
| ATP Buenos Aires MD | 2021/03/04 19:00 | Koepfer/Sousa v Bolelli/Gonzalez | 4-6,7-6,10-5 |