| Zimbabwe Premier Soccer League | 2019/04/13 13:00 | Harare City v Highlanders FC | L | 3-1 |
| Zimbabwe Premier Soccer League | 2018/11/04 13:00 | Highlanders FC v Harare City | W | 2-0 |
| Zimbabwe Premier Soccer League | 2018/06/02 13:00 | Harare City v Highlanders FC | W | 1-2 |
| Zimbabwe Cup | 2017/09/24 12:58 | Highlanders FC v Harare City | L | 1-2 |
| Zimbabwe Premier Soccer League | 2017/08/06 12:57 | Highlanders FC v Harare City | D | 0-0 |
| Zimbabwe Premier Soccer League | 2019/06/16 13:00 | Highlanders FC v Dynamos FC | W | 1-0 |
| Zimbabwe Premier Soccer League | 2019/06/08 13:00 | Yadah FC v Highlanders FC | L | 1-0 |
| Zimbabwe Premier Soccer League | 2019/06/02 13:00 | Highlanders FC v ZPC Kariba FC | W | 2-0 |
| Zimbabwe Premier Soccer League | 2019/05/26 13:00 | Telone FC v Highlanders FC | W | 0-1 |
| Zimbabwe Premier Soccer League | 2019/05/19 13:00 | Highlanders FC v Herentals FC | D | 0-0 |
| Zimbabwe Premier Soccer League | 2019/05/11 13:00 | Chicken Inn FC v Highlanders FC | L | 3-0 |
| Zimbabwe Premier Soccer League | 2019/05/05 13:00 | Highlanders FC v Hwange FC | D | 0-0 |
| Zimbabwe Premier Soccer League | 2019/04/27 13:00 | Mushowani Stars FC v Highlanders FC | D | 0-0 |
| Zimbabwe Premier Soccer League | 2019/06/15 13:00 | Harare City v Herentals FC | L | 1-2 |
| Zimbabwe Premier Soccer League | 2019/06/08 13:00 | Chicken Inn FC v Harare City | W | 1-2 |
| Zimbabwe Premier Soccer League | 2019/06/01 13:00 | Harare City v Hwange FC | W | 3-0 |
| Zimbabwe Premier Soccer League | 2019/05/26 13:00 | Mushowani Stars FC v Harare City | L | 2-1 |
| Zimbabwe Premier Soccer League | 2019/05/18 13:00 | Harare City v Triangle United | W | 2-1 |
| Zimbabwe Premier Soccer League | 2019/05/11 13:00 | Harare City v Bulawayo Chiefs FC | D | 0-0 |
| Zimbabwe Premier Soccer League | 2019/05/05 13:00 | CAPS United v Harare City | L | 1-0 |
| Zimbabwe Premier Soccer League | 2019/04/27 13:00 | Harare City v Black Rhinos FC | L | 1-2 |