| 2000 |
GLACIS UNITED |
Gibraltar United 6-5 d.c.r. (2-2) |
| 2001 |
LINCOLN RED IMPS |
Gibraltar United 3-1 |
| 2002 |
LINCOLN RED IMPS |
Gibraltar United 2-0 |
| 2003 |
MANCHESTER 62 |
Lincoln Red Imps 1-0 |
| 2004 |
LINCOLN RED IMPS |
Gibraltar United 3-1 |
| 2005 |
GLACIS UNITED |
Lincoln Red Imps 1-1 (decisa ai calci di rigore) |
| 2006 |
MANCHESTER 62 |
Lincoln Red Imps 4-2 d.c.r. (2-2) |
| 2007 |
LINCOLN RED IMPS |
Manchester 62 3-1 |
| 2008 |
LINCOLN RED IMPS |
Manchester 62 3-1 |
| 2009 |
LINCOLN RED IMPS |
Gibraltar United 3-1 |
| 2010 |
LINCOLN RED IMPS |
St Joseph's 1-0 |
| 2011 |
LINCOLN RED IMPS |
Glacis United 5-4 d.c.r. (1-1) |
| 2012 |
ST JOSEPH'S |
Lincoln Red Imps 2-0 |
| 2013 |
LINCOLN RED IMPS |
St Joseph's 11-10 d.c.r. (2-2) |
| 2014 |
LINCOLN RED IMPS |
Manchester 62 1-0 |
| 2015 |
LINCOLN RED IMPS |
Europa FC 3-2 d.t.s. |
| 2016 |
EUROPA FC |
Lincoln Red Imps - Europa FC 0-2 |
| 2017 |
LINCOLN RED IMPS |
Lincoln Red Imps - Europa FC 3-1 d.c.r. (2-2) |
| 2018 |
EUROPA FC |
Lincoln Red Imps - Europa FC 2-4 d.c.r. (1-1) |
| 2019 |
EUROPA FC |
Lincoln Red Imps - Europa FC 0-1 |
| 2020 |
non disputata per la pandemia di Covid-19 |
| 2021 |
EUROPA FC |
Lincoln Red Imps - Europa FC 1-3 |
| 2022 |
LINCOLN RED IMPS |
Lincoln Red Imps - Europa FC 1-0 |
| 2023 |
MAGPIES |
Lincoln Red Imps - Magpies 0-1 |
| 2024 |
ST JOSEPH'S |
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