Division Winners
The history of the CSSL Division winners are listed with the information available to the CSSL.
| Year | Division 1 | Division 2 | Division 3 | Division 4 | Division 5 |
| 2024 | Christchurch United | Avonhead AFC | Combine Brothers B | Sunnyside | = Not Played = |
| 2023 | Rovers FC | Hoon Hay | Northern Tigers | Prebbleton Wild Hogs | = Not Played = |
| 2022 | Rovers FC | Team Lotshampa | Dux de Lux B | St Albans Squires A | = Not Played = |
| 2021 | Fiji Rovers | Coastal Spirit Rovers | Dux de Lux A | Hoon Hay | St Albans Squires B |
| 2020 | St Albans Squires A | UCAFC Obikwa | Prebbleton Saints | Combine Brothers B | Woolston Foundry B |
| 2019 | Fiji Rovers | Lyttelton B | Christchurch Babasiga | Salamanders FC B | Avonhead C |
| 2018 | Glenbyre A | St Albans Squires A | Canterbury Allstars | Universities D | Dux de Lux B |
| 2017 | Treallus United | Glenbyre C | Combine Brothers A | Canterbury Fiji Rovers B | = Not Played = |
| 2016 | Avonhead B | Alvarados | Prebbleton Shamrocks | Universities | Team Lhotshampa |
| 2015 | Avonhead B | Prebbleton Rovers | Southern Districts Salamanders | Avonhead C | = Not Played = |
| 2014 | Woolston Foundry | Avonhead B | Glenbyre C | Cortados Salamanders | Coastal Spirit C |
| 2013 | Coastal Spirit A | Dux de Lux A | Prebbleton Saints | Prebbleton Rovers | St Albans Squires |
| 2012 | Avonhead A | Avonhead B | Avonhead C | Avonhead D | Cardrona-Alvarados |
| 2011 | Coastal Spirit A | Blue Shirts A | Avonhead B | Avonhead C | Prebbleton Saints |
| 2010 | Canterbury Fiji | Cardrona on Avon | Prebbleton Black Lions | Treallus United | Lyttelton B |
| 2009 | Coastal Spirit Rovers A | ||||
| 2008 | |||||
| 2007 | Coastal Spirit Rovers A | ||||
| 2006 | New Brighton | ||||
| 2005 | New Brighton | ||||
| 2004 | Glenbyre A | Lincoln B | Casino Jokers | Sandridge B | |
| 2003 | Glenbyre A | Lincoln | Casino Jokers | ||
| 2002 | Dux De Lux C | Plunders | |||
| 2001 | Transpotters | Dux De Lux D | |||
| 2000 | Heathcote D | New Brighton Rovers C | |||
| 1999 | Echo Records | Woolston Foundry | Heathcote D | ||
| 1998 | Hillsborough A | Paparua | |||
| 1997 | Dux De Lux A | Westpac Trust | |||
| 1996 | Heathcote A | Hillsborough C | |||
| 1995 | Heathcote A | Paparua United | |||
| 1994 | Avonhead A | Paparua | |||
| 1993 | Echo Records | Echo Records | |||
| 1992 | Hillsborough A | Dux De Lux C | |||
| 1991 | Hillsborough United | Hillsborough B | |||
| 1990 | Glenbyre A | Echo Records | |||
| 1989 | Glenbyre A | Woolston Foundry | |||
| 1988 | Hillsborough United | Transfitz | |||
| 1987 | Rheineck Glenbyre A | Ilam Hardies | |||
| 1986 | Woolston Foundry A | Burncastle Wanderers | |||
| 1985 | Foresters Tavern | Lyttelton Hotel | |||
| 1984 | Woolston Foundry A | Woolston Foundry B | |||
| 1983 | Foresters Tavern | Dux De Lux Dynamos | |||
| 1982 | DB Gladstone United | Air NZ | |||
| 1981 | DB Gladstone United | Wigram | |||
| 1980 | North Beach A | Avonhead C | |||
| 1979 | Ilam | ||||
| 1978 | |||||
| 1977 | Music Machine | ||||
| 1976 | Star and Garter | ||||
| 1975 | |||||
| 1974 | Whitcoulls |
