Player of Year Winners
The history of the CSSL Division Player of the Year winners are listed with the information available to the CSSL.
| Year | Division 1 | Division 2 | Division 3 | Division 4 | Division 5 |
| 2024 | Ben Cochrane (Joes Bower 11) | Sefo Rabuka (Canterbury Fiji Navua) | Sushil Sharma (Combine Brothers B) | Ben Williams (Combine Brothers X) | = None = |
| 2023 | Ryan Keenan (Rovers FC) | Simon Cornish (Hoon Hay) | Isaac Robertson (St Albans Squires) | Daniel Tsehaye (Thai Thunder) | = None = |
| 2022 | Ryan Keenan (Rovers FC) | Nishan Biswa (Lhotshampa FC) | Yuliktus Korain (Hoon Hay) | = Not Given = | = None = |
| 2021 | Ryan Keenan (Fiji Rovers) | Cedryc Schell (Coastal Spirit Rovers) | = Not Given = | Sunil Ban (Nepal United) | Abraham Rota (St Albans Squires B) |
| 2020 | Daniel DL Faz (Fiji Rovers) | Takahiro Inoue (Glenbyre B) | Mark Stone (Avonhead Redhawks) | = Not Given = | Rob Ackroyd (Woolston Foundry B) |
| 2019 | Ryan Keenan (Fiji Rovers) | Toru Akamine (Glenbyre B) | Iosefo Rabuka (Christchurch Babasiga) | = Not Given = | Josh Reid (Avonhead C) |
| 2018 | Paddy Devins (Fiji Rovers) | Wayne Enright (St Albans Squires) | Alan Brooks (Universities) | = Not Given = | = Not Given = |
| 2017 | Richie McCannon (Canterbury Fiji Rovers) | Geser Constancio (Glenbyre) | Sushil Sharma (Combine Brothers) | = Not Given = | = None = |
| 2016 | Maty Whittle (Avonhead) | Jamie Draper (Southern Districts Salamanders) | Ben Williams (Combine Brothers) | Ben Majendie (Ilam Hardies) | Aashish Rai (Team Lhotshampa) |
| 2015 | Matthew Palmer (Avonhead B) | John Boal (Prebbleton Rovers) | Rod Paiva (Glenbyre B) | David Scott (Avonhead C) | = None = |
| 2014 | Israel Inacio (Avonhead A) | Jeremias Freytes (Glenbyre A) | Stephen Shaw (Glenbyre C) | Andrew Welford (Cortados Salamanders) | Mick Hale (St Albans Squires B) |
| 2013 | Reuben Marshall (Coastal Spirit) | Bevan Jones (Southern Districts A) | Carl Sheehan (Christchurch United) | John Boal (Prebbleton) | Colin Bowden (Sunnyside C) |
| 2012 | Greg Milligan (Dux de Lux) | Chris Chen (Prebbleton G Force) | Sean Mortell (Golden Mile) | Adam Cox (Blue Shirts B) | John Dyskma (Sunnyside) |
| 2011 | Steve Lum (Glenbyre) | Mario Hammer (Blue Shirts) | Mat Whittle (Avonhead B) | Tim Campbell (Prebbleton) | Babu Chandar (Avonhead D) |
| = Missing | 2010 to 2005 = | ||||
| 2004 | Gavin Wright | T Weeber | Scott Hannah | Chris McPherson (Squires A) | John Taylor |
| 2003 | J Walsh | D Power | Steve Mulvey | Jon Bennett | |
| 2002 | Tony Green (New Brighton) | G Mills | Ty Butterfield | ||
| 2001 | Danny McNicoll | S Farrant | Rob Munro (Dux de Lux) | ||
| 2000 | Brent Wall (Glenbyre) | R Taylor | Paul Stokes (Avonhead) | ||
| 1999 | Dennis Alder (New Brighton) | Anton Witteman (Avonhead) | |||
| 1998 | John Hanson (Hillsborough) | ||||
| 1997 | K Mani | ||||
| 1996 | V Presad | ||||
| 1995 | J Mitchell | ||||
| 1994 | P Halliwell | ||||
| 1993 | W Quirke & A Velicias | ||||
| 1992 | W Quirke & S Richardson | ||||
| 1991 | |||||
| 1990 | R Isherwood (New Brighton) | ||||
| 1989 | Jeff Mclaughlan | ||||
| 1988 | Michael Kett | ||||
| 1987 | Wayne Burt | ||||
| 1986 | Ian Douglas | ||||
| 1985 | S Squires (Avonhead) | ||||
| 1984 | Des Duffy (Avonhead) | ||||
| 1983 | JK Field | ||||
| 1982 | TM Powell | ||||
| 1981 | |||||
| 1980 | W Yates | ||||
| 1979 | R Trowbridge (Woolston Foundry) | ||||
| 1978 | D Dwyer (Post Office Techs) | ||||
| 1977 | Jo Hitchcock | ||||
| 1976 | John Chaplin (Whitcoulls) | ||||
| 1975 | Les Whiteside (Christchurch Star) | ||||
| 1974 | D Chee (Royal George) |
