CSSL Trophy
The history of the CSSL Trophy winners and runners up are listed with the information available to the CSSL.
| Year | Winner | Score | Runner Up | Score |
| 2025 | Dux de Lux Old Boys | 1 | Prebbleton Wild Hogs | 0 |
| 2024 | Combine Brothers B | 6 | Prebbleton Wild Hogs | 2 |
| 2023 | St Albans Squires | =Default Win= | ||
| 2022 | Dux de Lux B | 3 | Avonhead B | 1 |
| 2021 | UCAFC Lyttelton | 4 | Team Lhotshampa | 2 |
| 2020 | Glenbyre B | 1 | Avonhead Redhawks | 0 |
| 2019 | Glenbyre B | 2 | Lyttelton B | 0 |
| 2018 | Glenbyre C | 2 | Universities D | 0 |
| 2017 | Glenbyre C | 3 | FC Lyttelton | 2 |
| 2016 | Southern Districts Salamanders | 2 | Glenbyre B | 1 |
| 2015 | Avonhead B | 3 | Glenbyre B | 2 |
| 2014 | Avonhead B | 5 | Cortados Salamanders | 1 |
| 2013 | Prebbleton Saints | 4 | Lyttelton Borough | 2 |
| 2012 | Avonhead B | 3 | Avonhead D | 2 |
| 2011 | Avonhead B | 4 | Avonhead C | 2 |
| 2010 | ||||
| 2009 | Prebbleton Shamrocks | |||
| 2008 | Coastal Spirit Rovers B | |||
| 2007 | Coastal Spirit Rovers B | |||
| 2006 | Avonhead B | |||
| 2005 | Glenbyre B | |||
| 2004 | New Brighton B | Glenbyre B | ||
| 2003 | ||||
| 2002 | Glenbyre B | Dux De Lux B | ||
| 2001 | Glenbyre B | Dux De Lux B | ||
| 2000 | Dux De Lux B | Heathcote B | ||
| 1999 | Dux De Lux C | Heathcote B | ||
| 1998 | Dux De Lux B | Hillsborough B | ||
| 1997 | Avonhead B | Brighton Rovers B | ||
| 1996 | Dux De Lux B | Echo Records B | ||
| 1995 | Echo Records B | Avonhead B | ||
| 1994 | Hillsborough B | Avonhead B | ||
| 1993 | Heathcote B | Hillsborough B | ||
| 1992 | Glenbyre B | Echo Records B | ||
| 1991 | Parklands Rovers B | Burncastle Wanderers B | ||
| 1990 | Dux De Lux B | |||
| 1989 | Dux De Lux C | Dux De Lux B | ||
| 1988 | Dux De Lux B | Dux De Lux C |
