| Date | Club | Course | Distance | Winner | Trainer | Driver | Time |
| 5th October 2019 | Northern Southland TC | Ascot Park | 2200 metres | Onesmartfella | Brent Shirley | Nathan Williamson | 2-49.2 |
| 22nd November 2019 | Invercargill HRC | Ascot Park | 2200 metres | Pembrook Playboy | Nathan Williamson | Nathan Williamson | 2-47.9 |
| 9th January | Northern Southland TC | Ascot Park | 2200 metres | | | | |
| 7th March | Northern Southland TC | Ascot Park | 2200 metres | | | | |
| 2nd May | Invercargill HRC | Ascot Park | 2200 metres | | | | |
| 6th June | Invercargill HRC | Ascot Park | 2200 metres | | | | |
| Southland Harness Awards - Ladyship Series Final Winners 2019/2020 | | | | | | | |
| Date | Club | Course | Distance | Winner | Trainer | Driver | Time |
| 12th October 2019 | Gore HRC | Gore | 2200 metres | Plutonium Lady | Mark Jones | Samantha Ottley | 2-43.2 |
| 7th December 2019 | Invercargill HRC | Ascot Park | 2200 metres | Held To Ransom | Jessie Alford | Brad Williamson | 2-41.7 |
| 16th January | Wyndham HRC | Young Quinn Raceway | 2400 metres | | | | |
| 14th March | Wyndham HRC | Young Quinn Raceway | 2400 metres | | | | |
| 21st April | Invercargill HRC | Ascot Park | 2200 metres | | | | |
| 1st June | Invercargill HRC | Ascot Park | 2200 metres | | | | |
| Aldebaran Park Gold Chip Series Final Winners 2019/2020 | | | | | | | |
| Date | Club | Course | Distance | Winner | Trainer | Driver | Time |
| 20th October 2019 | Riverton TC | Ascot Park | 2700 metres | Tweedledee | Lyndon Bond | Nathan Williamson | 3-35.2 |
| 21st December 2019 | Wairio TC | Central Southland Raceway | 2400 metres | Cracker Hill | Brad Williamson | Kerryn Tomlinson | 3-03.1 |
| 30th January | Wyndham HRC | Young Quinn Raceway | 2400 metres | | | | |
| 1st March | Invercargill HRC | Ascot Park | 2200 metres | | | | |
| 18th April | Winton HRC | Central Southland Raceway | 2400 metres | | | | |
| 6th June | Invercargill HRC | Ascot Park | 2200 metres | | | | |
