| Botswana Premier League | 2019/03/12 17:00 | Security Systems FC v Orapa United | W | 1-0 |
| Botswana Premier League | 2018/11/02 17:00 | Orapa United v Security Systems FC | L | 2-0 |
| Botswana Premier League | 2019/09/17 17:00 | BR Highlanders v Security Systems FC | W | 1-2 |
| Botswana Premier League | 2019/09/13 17:00 | Notwane FC v Security Systems FC | W | 0-1 |
| Botswana Premier League | 2019/08/31 13:30 | Security Systems FC v Morupule Wanderers FC | W | 1-0 |
| Botswana Premier League | 2019/05/24 17:00 | BDF XI v Security Systems FC | D | 1-1 |
| Botswana Premier League | 2019/05/04 17:00 | Security Systems FC v Miscellaneous | D | 0-0 |
| Botswana Premier League | 2019/05/01 17:00 | Black Forest v Security Systems FC | W | 0-5 |
| Botswana Premier League | 2019/04/24 17:00 | Security Systems FC v Shooting Stars | W | 2-1 |
| Botswana Premier League | 2019/04/09 17:00 | Security Systems FC v Sankoyo Bush Bucks | W | 2-1 |
| Botswana Premier League | 2019/09/18 17:00 | Orapa United v Gilport Lions | D | 2-2 |
| Botswana Premier League | 2019/09/14 16:00 | Township Rollers v Orapa United | L | 3-1 |
| Botswana Premier League | 2019/09/01 13:30 | Tafic FC v Orapa United | W | 0-1 |
| Botswana Premier League | 2019/05/25 13:30 | Black Forest v Orapa United | W | 0-4 |
| Botswana FA Cup | 2019/05/18 14:02 | Botswana Police XI SC v Orapa United | D | 1-1 |
| Botswana Premier League | 2019/05/04 13:30 | Orapa United v Notwane FC | W | 3-2 |
| Botswana Premier League | 2019/05/01 14:00 | Jwaneng Galaxy FC v Orapa United | D | 0-0 |
| Botswana Premier League | 2019/04/23 16:00 | Miscellaneous v Orapa United | W | 0-6 |