Stadium: Court 1 Round: 28 Ground: Hardcourt outdoor
| ATP Newport | 2019/07/15 17:55 | Ivo Karlovic v Guido Andreozzi | 6-7,6-7 |
| Wimbledon | 2019/07/03 11:20 | Ivo Karlovic v Thomas Fabbiano | 3-6,7-6,3-6,7-6,4-6 |
| Wimbledon | 2019/07/01 13:55 | Andrea Arnaboldi v Ivo Karlovic | 4-6,4-6,6-7 |
| ATP Queens | 2019/06/16 11:40 | Ivo Karlovic v James Ward | 6-7,4-6 |
| ATP Queens | 2019/06/15 11:00 | Ivo Karlovic v Peter Polansky | 6-3,7-5 |
| Challenger Nottingham | 2019/06/14 11:00 | Evgeny Donskoy v Ivo Karlovic | 6-3,6-7,7-6 |
| Challenger Nottingham | 2019/06/12 15:00 | Stefano Napolitano v Ivo Karlovic | 6-7,6-4,3-6 |
| Challenger Surbiton | 2019/06/08 09:30 | Viktor Troicki v Ivo Karlovic | 6-2,5-7,7-6 |
| Challenger Tampere | 2019/07/24 11:15 | Christopher O'Connell v Pedja Krstin | 4-6,6-1,3-6 |
| Challenger Tampere | 2019/07/23 08:55 | Christopher O'Connell v Khumoyun Sultanov | 7-5,6-4 |
| Challenger San Benedetto | 2019/07/17 19:15 | Alessandro Giannessi v Christopher O'Connell | 7-6,6-3 |
| Challenger San Benedetto | 2019/07/16 10:00 | Christopher O'Connell v Riccardo Balzerani | 7-5,6-3 |
| ITF M25 Casinalbo | 2019/07/14 15:00 | Christian Lindell v Christopher O'Connell | 7-6,5-7,6-3 |
| ITF M25 Casinalbo | 2019/07/13 16:00 | Gijs Brouwer v Christopher O'Connell | 4-6,6-4,6-7 |
| ITF M25 Casinalbo | 2019/07/12 12:05 | Christopher O'Connell v Juan Pablo Varillas | 6-3,1-6,6-4 |
| ITF M25 Casinalbo | 2019/07/11 10:30 | Christopher O'Connell v Giovanni Fonio | 6-1,6-2 |