| 2019 Davis Cup | 11/22 09:30 | - | [40] Filip Krajinovic v Andrey Rublev [23] | 1-6,2-6 | |
| 2019 Davis Cup | 11/21 10:00 | 1 | [29] Jo-Wilfried Tsonga v Filip Krajinovic [40] | 5-7,6-7 | |
| 2019 Davis Cup | 11/20 10:00 | 1 | [40] Filip Krajinovic v Yuichi Sugita [104] | 6-2,6-4 | |
| ATP Basel | 10/25 18:00 | 27 | [7] Stefanos Tsitsipas v Filip Krajinovic [46] | 3-6,6-4,6-4 | |
| ATP Basel | 10/24 20:20 | 26 | [46] Filip Krajinovic v Fabio Fognini [12] | 6-2,6-4 | |
| ATP Basel | 10/23 12:25 | 25 | [39] Laslo Djere v Filip Krajinovic [46] | 1-6,4-6 | |
| ATP Stockholm | 10/20 13:00 | 29 | [34] Denis Shapovalov v Filip Krajinovic [60] | 6-4,6-4 | |
| ATP Stockholm | 10/19 13:00 | 28 | [60] Filip Krajinovic v Pablo Carreno-Busta [35] | 4-6,6-3,6-3 | |
| ATP Stockholm | 10/18 12:00 | 27 | [60] Filip Krajinovic v Yoshihito Nishioka [74] | 6-3,6-4 | |
| ATP Stockholm | 10/16 19:05 | 26 | [43] Daniel Evans v Filip Krajinovic [60] | 5-7,6-2,3-6 | |
| ATP Stockholm | 10/15 18:30 | 25 | [60] Filip Krajinovic v Casper Ruud [59] | 6-3,7-5 | |
| ATP Shanghai | 10/06 06:30 | 24 | [62] Joao Sousa v Filip Krajinovic [49] | 2-6,6-4,7-6 | |
| ATP Tokyo | 10/01 05:05 | 25 | [45] Radu Albot v Filip Krajinovic [49] | 6-3,7-5 | |
| ATP Metz | 09/20 16:00 | 27 | [49] Filip Krajinovic v Lucas Pouille [26] | 6-4,5-7,2-6 | |
| ATP Metz | 09/18 19:15 | 26 | [35] Fernando Verdasco v Filip Krajinovic [49] | 6-3,4-6,3-6 | |
| ATP Metz | 09/16 17:30 | 25 | [89] Peter Gojowczyk v Filip Krajinovic [49] | 5-7,4-6 | |
| US Open | 08/27 18:40 | 23 | [52] Filip Krajinovic v Cedrik-Marcel Stebe [256] | 3-6,6-4,4-6,6-7 | |
| ATP Winston-Salem | 08/22 00:30 | 26 | [51] Filip Krajinovic v Frances Tiafoe [52] | Retired | |
| ATP Winston-Salem | 08/20 19:50 | 25 | [51] Filip Krajinovic v Tomas Berdych [101] | 3-6,7-5,6-1 | |
| ATP Hamburg | 07/26 13:05 | 27 | [58] Filip Krajinovic v Alexander Zverev [5] | 6-2,5-7,2-6 | |
| ATP Hamburg | 07/25 09:30 | 26 | [58] Filip Krajinovic v Martin Klizan [62] | 6-7,7-5,6-1 | |
| ATP Hamburg | 07/23 14:40 | 25 | [31] Laslo Djere v Filip Krajinovic [58] | 3-6,3-6 | |
| ATP Umag | 07/17 14:30 | 26 | [207] Attila Balazs v Filip Krajinovic [58] | 6-3,6-7,7-6 | |
| ATP Umag | 07/16 18:30 | 25 | [112] Taro Daniel v Filip Krajinovic [58] | 5-7,6-7 | |
| Wimbledon | 07/02 12:55 | 23 | [130] Dominik Koepfer v Filip Krajinovic [52] | 6-3,4-6,7-6,6-1 | |
| Boodles Challenge | 06/28 13:30 | 1 | [48] Grigor Dimitrov v Filip Krajinovic [51] | 6-3,7-6 | |
| Boodles Challenge | 06/27 16:40 | 1 | [51] Filip Krajinovic v Martin Klizan [54] | 6-4,7-6 | |
| French Open | 06/01 10:10 | 25 | [6] Stefanos Tsitsipas v Filip Krajinovic [60] | 7-5,6-3,6-7,7-6 | |
| French Open | 05/29 11:50 | 24 | [76] Roberto Carballes Baena v Filip Krajinovic [60] | 4-6,4-6,7-6,6-3,6-8 | |
| French Open | 05/27 09:00 | 23 | [60] Filip Krajinovic v Frances Tiafoe [34] | 6-2,4-6,6-3,3-6,6-0 |