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| | Southern Country Cups Handicap | | | | | | | | |
| Year | Winner | Driver | Trainer | Track | Distance | Time | Winning Sire | Second |
| 1 | 2001 | Bonnie Lass | Brent Barclay | BD McIntyre | Invercargill | 2700 | 3-30.2 | Camtastic | Pickapocket |
| 2 | 2002 | Shortys Girl | Allan Beck | AR Beck | Invercargill | 2700 | 3-26.2 | New York Motoring | Bonnie Lass |
| 3 | 2003 | Whanau | Brent Barclay | HW Skinner | Invercargill | 2700 | 3-28.3 | Sands A Flyin | Merle's Boy |
| 4 | 2004 | Howard Bromac | Kirk Larsen | KN Larsen | Invercargill | 2700 | 3-33.5 | Falcon Seelster | Skinstaad |
| 5 | 2005 | The Jaccka | Brent Barclay | JW Adams | Invercargill | 2700 | 3-36.0 | Live Or Die | Nursemaid |
| 6 | 2006 | Chesterton | Brent Shirley | GR Shirley | Invercargill | 2700 | 3-23.9 | Christian Cullen | Mr PB |
| 7 | 2007 | Bondy | Robin Butt | DJ and Mrs CM Butt | Invercargill | 2700 | 3-34.6 | Live Or Die | Sand Express |
| 8 | 2008 | Here Comes Soky | Nathan Williamson | BA Lilley | Invercargill | 2700 | 3-27.5 | Soky's Atom | Tartan Rover |
| 9 | 2009 | Russlands | Jordan Compain | AFH Hunter | Invercargill | 2700 | 3-30.9 | Live Or Die | Bigtime Blue Jeans |
| 10 | 2010 | Beaudiene Bad Babe | Dexter Dunn | MG Brown | Invercargill | 2700 | 3-27.0 | Badlands Hanover | Best Legacy |
| 11 | 2011 | Flying Diamonds | Dexter Dunn | Tony Stratford | Invercargill | 2700 | 3-27.2 | Falcon Seelster | Vi Et Animo |
| 12 | 2012 | Franco Ledger | Hamish Hunter | AFH Hunter | Invercargill | 2700 | 3-25.5 | Falcon Seelster | Donthavtime |
| 13 | 2013 | Jimmy Johnstone | John Hay | JC Hay | Invercargill | 2700 | 3-25.0 | P-Forty Seven | Canardly Lover |
| 14 | 2014 | Pemberton Shard | Dexter Dunn | Brad Mowbray | Invercargill | 2700 | 3-21.2 | Christian Cullen | Belkmyster |
| 15 | 2015 | Al Raza | Tim Williams | Geoff and Jude Knight | Invercargill | 2700 | 3-24.4 | Gotta Go Cullect | Sheeza Shark |
| 16 | 2016 | Costa Del Magnifico | Nathan Williamson | Brent Shirley | Invercargill | 2700 | 3-24.2 | Mach Three | I'm Full Of Excuses |
| 17 | 2017 | Bettor Ops | Kirk Larsen | Kirk Larsen | Invercargill | 2700 | 3-24.3 | Bettor's Delight | Glenferrie Classic |
| 18 | 2018 | Swamp Major | Sam Ottley | Regan Todd | Invercargill | 2700 | 3-25.2 | Art Major | Mighty Santanna |
| 19 | 2019 | Vintage Cheddar | Brad Williamson | Alister Black | Invercargill | 2700 | 3-27.1 | Betterthancheddar | Smokin By |
| 2020 | Not Held | | | | | | | |
| 20 | 2021 | Pembrook Playboy | Nathan Williamson | Nathan Williamson | Invercargill | 2700 | 3-22.7 | Bettors Delight | Deux Ex |
