 
                     
        | Time | League | Home Team | Score | Away Team | 
|---|---|---|---|---|
| 2024-11-23 
                                    2 : 3
                                 | New Zealand Football Championship | Wellington Olympic | 2 : 3 
                                    2 : 3
                                 | Napier City Rovers | 
| 2024-11-17 
                                    3 : 1
                                 | New Zealand Football Championship | Wellington Phoenix Reserve | 3 : 1 
                                    3 : 1
                                 | Wellington Olympic | 
| 2024-11-08 
                                    4 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 4 : 1 
                                    4 : 1
                                 | Western Suburbs | 
| 2024-11-02 
                                    1 : 2
                                 | New Zealand Football Championship | Wellington Olympic | 1 : 2 
                                    1 : 2
                                 | Birkenhead United | 
| 2024-10-26 
                                    2 : 3
                                 | New Zealand Football Championship | Western Springs AFC | 2 : 3 
                                    2 : 3
                                 | Wellington Olympic | 
| 2024-10-19 
                                    2 : 2
                                 | New Zealand Football Championship | Cashmere Technical | 2 : 2 
                                    2 : 2
                                 | Wellington Olympic | 
| 2024-10-12 
                                    4 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 4 : 1 
                                    4 : 1
                                 | Eastern Suburbs AFC | 
| 2024-10-05 
                                    0 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 0 : 1 
                                    0 : 1
                                 | Auckland City | 
| 2024-09-28 
                                    0 : 0
                                 | New Zealand Football Championship | Coastal Spirit | 0 : 0 
                                    0 : 0
                                 | Wellington Olympic | 
| 2024-03-16 
                                    3 : 3
                                 | OFC Champions League | Wellington Olympic | 3 : 3 
                                    3 : 3
                                 | Auckland City | 
| 2024-03-09 
                                    1 : 0
                                 | OFC Champions League | Auckland City | 1 : 0 
                                    1 : 0
                                 | Wellington Olympic | 
| 2024-03-03 
                                    3 : 0
                                 | International Club Friendly | Wellington Olympic | 3 : 0 
                                    3 : 0
                                 | Christchurch United | 
| 2023-11-19 
                                    4 : 2
                                 | New Zealand Football Championship | Wellington Olympic | 4 : 2 
                                    4 : 2
                                 | Wellington Phoenix Reserve | 
| 2023-11-12 
                                    1 : 3
                                 | New Zealand Football Championship | Auckland City | 1 : 3 
                                    1 : 3
                                 | Wellington Olympic | 
| 2023-11-04 
                                    5 : 2
                                 | New Zealand Football Championship | Wellington Olympic | 5 : 2 
                                    5 : 2
                                 | Christchurch United | 
| 2023-10-28 
                                    2 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 2 : 1 
                                    2 : 1
                                 | Petone FC | 
| 2023-10-21 
                                    1 : 3
                                 | New Zealand Football Championship | Auckland United | 1 : 3 
                                    1 : 3
                                 | Wellington Olympic | 
| 2023-10-14 
                                    2 : 2
                                 | New Zealand Football Championship | Wellington Olympic | 2 : 2 
                                    2 : 2
                                 | Eastern Suburbs AFC | 
| 2023-10-07 
                                    3 : 3
                                 | New Zealand Football Championship | Cashmere Technical | 3 : 3 
                                    3 : 3
                                 | Wellington Olympic | 
| 2023-09-30 
                                    8 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 8 : 1 
                                    8 : 1
                                 | Napier City Rovers | 
| 2023-09-24 
                                    2 : 5
                                 | New Zealand Football Championship | Manuel Wa | 2 : 5 
                                    2 : 5
                                 | Wellington Olympic | 
| 2023-03-18 
                                    5 : 3
                                 | OFC Champions League | Auckland City | 5 : 3 
                                    5 : 3
                                 | Wellington Olympic | 
| 2023-03-11 
                                    1 : 1
                                 | OFC Champions League | Wellington Olympic | 1 : 1 
                                    1 : 1
                                 | Auckland City | 
| 2022-11-27 
                                    1 : 4
                                 | New Zealand Football Championship | Miramar Rangers | 1 : 4 
                                    1 : 4
                                 | Wellington Olympic | 
| 2022-11-19 
                                    7 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 7 : 1 
                                    7 : 1
                                 | Christchurch United | 
| 2022-11-13 
                                    1 : 1
                                 | New Zealand Football Championship | Wellington Phoenix Reserve | 1 : 1 
                                    1 : 1
                                 | Wellington Olympic | 
| 2022-11-05 
                                    3 : 1
                                 | New Zealand Football Championship | Wellington Olympic | 3 : 1 
                                    3 : 1
                                 | Auckland United | 
| 2022-10-29 
                                    2 : 5
                                 | New Zealand Football Championship | Napier City Rovers | 2 : 5 
                                    2 : 5
                                 | Wellington Olympic | 
| 2022-10-22 
                                    2 : 0
                                 | New Zealand Football Championship | Wellington Olympic | 2 : 0 
                                    2 : 0
                                 | Birkenhead United | 
| 2022-10-16 
                                    0 : 3
                                 | New Zealand Football Championship | Cashmere Technical | 0 : 3 
                                    0 : 3
                                 | Wellington Olympic |