The Legends Trophy, Sponsored by Legends Bar. Started as the Ambassador Trophy in 1996/97, Changed to the Northern Hotel Trophy for 2010/11, then becoming the Riley's Trophy in 14/15 before becoming the Legends Trophy in 2019/20.
| Legends Trophy | ||||
| Year | Winner | Runner-up | ||
| 2022 / 23 | White Cockade | Lord Byron | ||
| 2021 / 22 | Staging Post | Kings Bar B | ||
| 2020 / 21 | No Season Due to Covid-19 | |||
| 2019 / 20 | Butchers Arms | Mounthooly | ||
| Changed to Legends Trophy '19 | ||||
| 2018 / 19 | Grampian Bar B | Portals | ||
| 2017 / 18 | Langdykes | Scotia Bar | ||
| 2016 / 17 | McNasty's B | Riley's B | ||
| 2015 / 16 | McNasty's B | East Neuk Lounge | ||
| 2014 / 15 | Butchers Arms B | Kings Bar | ||
| Changed to Riley's Trophy '14 | ||||
| 2013 / 14 | Kings Bar | Crown & Anchor | ||
| 2012 / 13 | Devanha Lounge | Victoria Lounge | ||
| 2011 / 12 | Cove Rangers SC | Enigma | ||
| 2010 / 11 | Bon Accord GC | Brig O' Dee | ||
| Changed to Northern Hotel Trophy '10 | ||||
| 2009 / 10 | Black Dog | Grays Inn Lounge | ||
| 2008 / 09 | Fourmile House | Sunnybank Club | ||
| 2007 / 08 | Cloverleaf Hotel | Kittybrewster | ||
| 2006 / 07 | Mither Tap | Cloverleaf Hotel | ||
| 2005 / 06 | Tap Room | Campbells | ||
| 2004 / 05 | White Cockade | East End Club | ||
| 2003 / 04 | Clares Bar | Broadhill Bar | ||
| 2002 / 03 | White Horse | Kings Bar B | ||
| 2001 / 02 | Harbour Bar | Hawthorn | ||
| 2000 / 01 | Lord Byron | Harbour Bar | ||
| 1999 / 00 | Nicky Tams | St Andrews | ||
| 1998 / 99 | Auchmill Inn | Kings Bar | ||
| 1997 / 98 | Greentrees | St Clements | ||
| 1996 / 97 | Fountain | Ally Dawson | ||
| Started as Ambassor Trophy '96 | ||||