| Challenger Chicago | 09/05 15:00 | 25 | Andreas Seppi v Ivo Karlovic | Cancelled | |
| US Open | 08/23 21:30 | 45 | [345] Collin Altamirano v Ivo Karlovic [137] | 7-5,6-4 | |
| US Open | 08/22 21:35 | 44 | [334] Illya Marchenko v Ivo Karlovic [137] | 3-6,6-7 | |
| ATP Cincinnati Qual | 08/12 18:40 | 46 | [112] Hubert Hurkacz v Ivo Karlovic [111] | 7-6,7-6 | |
| ATP Cincinnati Qual | 08/11 23:00 | 45 | [111] Ivo Karlovic v Taro Daniel [78] | 7-6,6-3 | |
| ATP Los Cabos | 07/31 04:15 | 25 | [113] Ivo Karlovic v Elias Ymer [108] | 4-6,3-6 | |
| ATP Atlanta | 07/23 23:00 | 25 | [117] Ivo Karlovic v Donald Young [230] | 6-2,6-7,6-7 | |
| ATP Newport | 07/18 17:45 | 26 | [156] Dudi Sela v Ivo Karlovic [110] | 7-6,6-7,6-2 | |
| ATP Newport | 07/17 19:10 | 25 | [110] Ivo Karlovic v Alex De Minaur [68] | 6-7,7-6,7-5 | |
| Wimbledon | 07/04 13:20 | 24 | [112] Ivo Karlovic v Jan-Lennard Struff [64] | 7-6,6-3,6-7,6-7,11-13 | |
| Wimbledon | 07/02 12:50 | 23 | [112] Ivo Karlovic v Mikhail Youzhny [102] | 4-6,7-5,7-6,6-3 | |
| ATP Halle Qual | 06/16 09:00 | 64 | [94] Lukas Lacko v Ivo Karlovic [90] | 7-6,7-6 | |
| ATP Hertogenbosch | 06/11 12:40 | 25 | [44] Robin Haase v Ivo Karlovic [90] | 7-6,6-7,6-3 | |
| French Open | 05/27 12:25 | 23 | [93] Ivo Karlovic v Corentin Moutet [143] | 6-7,2-6,6-7 | |
| ATP Geneva | 05/21 13:20 | 25 | [93] Ivo Karlovic v Peter Gojowczyk [49] | 6-7,6-4,6-7 | |
| ATP München | 05/01 11:00 | 25 | [34] Philipp Kohlschreiber v Ivo Karlovic [82] | 7-5,6-4 | |
| ATP Barcelona | 04/24 16:20 | 25 | Ivo Karlovic v Roberto Bautista-Agut | 7-6,2-6,4-6 | |
| ATP Barcelona | 04/23 13:45 | 24 | [211] Tommy Robredo v Ivo Karlovic [75] | 7-6,6-7,4-6 | |
| ATP Houston | 04/14 19:00 | 28 | [88] Ivo Karlovic v Tennys Sandgren [56] | 6-7,6-7 | |
| ATP Houston | 04/13 19:35 | 27 | [88] Ivo Karlovic v Nick Kyrgios [24] | 3-6,6-2,6-3 | |
| ATP Houston | 04/11 18:45 | 26 | [122] Denis Kudla v Ivo Karlovic [88] | 5-7,5-7 | |
| ATP Houston | 04/10 17:00 | 25 | [111] Taro Daniel v Ivo Karlovic [88] | 6-7,4-6 | |
| ATP Miami | 03/21 21:30 | 23 | [79] Ivo Karlovic v Vasek Pospisil [77] | 6-7,6-7 | |
| ATP Indian Wells | 03/08 20:50 | 23 | Ivo Karlovic v Maximilian Marterer | 7-6,6-7,3-6 | |
| ATP Delray Beach | 02/20 20:10 | 25 | Denis Shapovalov v Ivo Karlovic | 7-5,7-6 | |
| ATP New York | 02/16 20:50 | 27 | Ivo Karlovic v Sam Querrey | 6-7,6-7 | |
| ATP New York | 02/15 20:00 | 26 | Ryan Harrison v Ivo Karlovic | 4-6,4-6 | |
| ATP New York | 02/12 22:25 | 25 | Jared Donaldson v Ivo Karlovic | 4-6,6-7 | |
| ATP Quito | 02/08 19:20 | 26 | Corentin Moutet v Ivo Karlovic | 7-5,6-7,7-6 | |
| ATP Quito | 02/07 17:00 | 25 | Ernesto Escobedo v Ivo Karlovic | 4-6,7-6,6-7 |