Weather: Cloudy Pitch: Good Round: 23
| Botswana Premier League | 2018/11/02 17:00 | Orapa United v Security Systems FC | L | 2-0 |
| Botswana Premier League | 2018/11/29 17:00 | Shooting Stars v Security Systems FC | D | 1-1 |
| Botswana Premier League | 2018/11/11 13:45 | Security Systems FC v Prisons XI Gaborone | L | 0-1 |
| Botswana Premier League | 2018/11/02 17:00 | Orapa United v Security Systems FC | L | 2-0 |
| Botswana Premier League | 2018/10/27 13:45 | Security Systems FC v Gaborone United | W | 1-0 |
| Botswana Premier League | 2018/10/23 17:00 | Security Systems FC v Township Rollers | L | 0-1 |
| Botswana Premier League | 2018/10/20 14:00 | BR Highlanders v Security Systems FC | L | 3-2 |
| Botswana Premier League | 2018/10/07 13:45 | Centre Chiefs v Security Systems FC | L | 2-1 |
| Botswana Premier League | 2018/09/26 17:00 | Security Systems FC v Extension Gunners | W | 2-1 |
| Botswana Top 8 Cup | 2018/12/09 14:00 | BDF XI v Orapa United | D | 0-0 |
| CAF Confederations Cup | 2018/12/05 17:00 | Orapa United v Petro Luanda | L | 0-2 |
| CAF Confederations Cup | 2018/11/27 15:00 | Petro Luanda v Orapa United | L | 4-0 |
| Botswana Premier League | 2018/11/10 13:45 | Township Rollers v Orapa United | W | 1-2 |
| Botswana Premier League | 2018/11/07 16:00 | Orapa United v Jwaneng Galaxy FC | W | 1-0 |
| Botswana Premier League | 2018/11/02 17:00 | Orapa United v Security Systems FC | W | 2-0 |
| Botswana Premier League | 2018/10/27 14:00 | Prisons XI Gaborone v Orapa United | W | 0-1 |
| Botswana Premier League | 2018/10/23 16:00 | Orapa United v Black Forest | D | 1-1 |