Head to Head
| New Zealand Central League | 2020/06/21 02:00 | Wairarapa United v Wellington Olympic | L | 3-2 |
| New Zealand Central League | 2019/08/07 06:29 | Wellington Olympic v Wairarapa United | W | 5-3 |
| New Zealand Central League | 2019/03/30 03:57 | Wairarapa United v Wellington Olympic | W | 0-10 |
| New Zealand Cup | 2018/06/23 05:48 | Wellington Olympic v Wairarapa United | L | 0-5 |
| New Zealand Central League | 2018/04/02 05:47 | Wellington Olympic v Wairarapa United | W | 2-1 |
Home History
| New Zealand Central League | 2020/08/01 03:45 | Wellington Olympic v Miramar Rangers | L | 1-4 |
| New Zealand Central League | 2020/07/25 03:00 | Petone FC v Wellington Olympic | W | 0-4 |
| New Zealand Central League | 2020/06/27 03:45 | Wellington Olympic v Waterside Karori | W | 8-1 |
| New Zealand Central League | 2020/06/21 02:00 | Wairarapa United v Wellington Olympic | L | 3-2 |
| New Zealand Central League | 2020/06/13 03:45 | Wellington Olympic v Napier City Rovers | L | 1-2 |
| New Zealand Central League | 2019/08/10 05:50 | Wellington Olympic v Waterside Karori | W | 1-0 |
| New Zealand Central League | 2019/08/07 06:29 | Wellington Olympic v Wairarapa United | W | 5-3 |
| New Zealand Central League | 2019/07/27 02:28 | North Wellington AFC v Wellington Olympic | L | 2-0 |
Away History
| New Zealand Central League | 2020/08/02 02:00 | Wairarapa United v Lower Hutt City | W | 1-0 |
| New Zealand Central League | 2020/06/28 02:30 | Western Suburbs v Wairarapa United | L | 4-0 |
| New Zealand Central League | 2020/06/21 02:00 | Wairarapa United v Wellington Olympic | W | 3-2 |
| New Zealand Central League | 2019/08/17 03:45 | Wairarapa United v Lower Hutt City | L | 0-5 |
| New Zealand Central League | 2019/08/07 06:29 | Wellington Olympic v Wairarapa United | L | 5-3 |
| New Zealand Central League | 2019/07/28 02:01 | Western Suburbs v Wairarapa United | L | 3-0 |
| New Zealand Central League | 2019/07/20 02:29 | Wellington United v Wairarapa United | D | 3-3 |
| New Zealand Central League | 2019/07/13 02:32 | Stop Out v Wairarapa United | L | 4-2 |