| Brian Jeffrey Memorial Over 50s | 2024 | Neil Wood | Heworth | 1 | 0 | Mo Mohammed | Fulford | 2023-24 |
| Brian Jeffrey Memorial Over 50s | 2023 | Phil Cooke | Fulford | 1 | 0 | Tim Fillingham | Bootham | 2022-23 |
| Brian Jeffrey Memorial Over 50s | 2022 | Neil Wood | Heworth | 1 | 0 | Trevor Ventress | Acomb | 2021-22 |
| Brian Jeffrey Memorial Over 50s | 2020 | Andy Wade | Acomb | 1 | 0 | Jeff Keen | Acomb | 2019-20 |
| Brian Jeffrey Memorial Over 50s | 2019 | Alan Reed | Fulford | 1 | 0 | Bob Smith | Fulford | 2018-19 |
| Brian Jeffrey Memorial Over 50s | 2018 | Andy Wade | Acomb | 1 | 0 | Mo Mohammed | Fulford | 2017-18 |
| Brian Jeffrey Memorial Over 50s | 2017 | Bob Smith | Bootham | 1 | 0 | Phil Cooke | Fulford | 2016-17 |
| Brian Jeffrey Memorial Over 50s | 2016 | J.McCready | Heworth | 1 | 0 | Jeff Brown | Bootham | 2015-16 |
| Brian Jeffrey Memorial Over 50s | 2015 | Jeff Keen | Acomb | 1 | 0 | Keith Watkinson | Heworth | 2014-15 |
| Brian Jeffrey Memorial Over 50s | 2014 | J.McCready | Heworth | 1 | 0 | Trevor Ventress | Acomb | 2013-14 |
| Brian Jeffrey Memorial Over 50s | 2013 | Bob Smith | Fulford | 1 | 0 | Lol Barnes | Bootham | 2012-13 |
| Brian Jeffrey Memorial Over 50s | 2012 | Bob Smith | Fulford | 1 | 0 | Geoff Robinson | Fulford | 2011-12 |
| Brian Jeffrey Construction Over 50s | 2011 | John Sherlock | Heworth | 1 | 0 | Colin Robinson | Bootham | 2010-11 |
| Brian Jeffrey Construction Over 50s | 2010 | Vic Gamble | Heworth | 1 | 0 | Richard Williamson | Malton | 2009-10 |
| Brian Jeffrey Construction Over 50s | 2009 | Bob Smith | Fulford | 1 | 0 | Vic Gamble | Heworth | 2008-09 |
| Brian Jeffrey Construction Over 50s | 2008 | Colin Robinson | Bootham | 1 | 0 | Bob Smith | Fulford | 2007-08 |
| Brian Jeffrey Construction Over 50s | 2007 | Bob Smith | Fulford | 1 | 0 | Ken Taylor | Bootham | 2006-07 |
| Brian Jeffrey Construction Over 50s | 2006 | Alan Reed | Fulford | 1 | 0 | Jeff Brown | Fulford | 2005-06 |
| Brian Jeffrey Construction Over 50s | 2005 | Ken Taylor | Bootham | 1 | 0 | Ray Robson | Fulford | 2004-05 |
| Brian Jeffrey Construction Over 50s | 2004 | Ken Taylor | Bootham | 1 | 0 | Alan Reed | Fulford | 2003-04 |
| Brian Jeffrey Construction Over 50s | 2003 | Ken Taylor | Bootham | 1 | 0 | Colin Richardson | Heworth | 2002-03 |
| Hunter Motor Spares Over 50s | 2002 | Ken Taylor | Bootham | 1 | 0 | Peter Webster | Heworth | 2001-02 |
| Hunter Motor Spares Over 50s | 2001 | Brian Birch | Heworth | 1 | 0 | Brian Henry | Acomb | 2000-01 |
| Hunter Motor Spares Over 50s | 2000 | Trevor Ventress | Acomb | 1 | 0 | Keith Watkinson | Heworth | 1999-00 |
| Hunter Motor Spares Over 50s | 1999 | Ken Taylor | Bootham | 1 | 0 | Colin Robinson | Bootham | 1998-99 |
| Hunter Motor Spares Over 50s | 1998 | Geoff Robinson | Fulford | 1 | 0 | Trevor Ventress | Acomb | 1997-98 |
| Hunter Motor Spares Over 50s | 1997 | Ken Taylor | Bootham | 1 | 0 | Colin Robinson | Bootham | 1996-97 |
| Hunter Motor Spares Over 50s | 1996 | Ken Taylor | Bootham | 1 | 0 | Bob Ventress | Acomb | 1995-96 |
| Hunter Motor Spares Over 50s | 1995 | Barney Willis | Acomb | 1 | 0 | George Lyth | Bootham | 1994-95 |
| Hunter Motor Spares Over 50s | 1994 | Sid Travis | Bootham | 1 | 0 | Mick Frampton | Fulford | 1993-94 |
| Hunter Motor Spares Over 50s | 1993 | Bob Ventress | Bootham | 1 | 0 | George Tingle | Bootham | 1992-93 |
| Hunter Motor Spares Over 50s | 1992 | Brian Jeffrey | Acomb | 1 | 0 | Bob Ventress | Acomb | 1991-92 |
| Hunter Motor Spares Over 50s | 1991 | Peter Webster | Heworth | 1 | 0 | Keith Watkinson | Heworth | 1990-91 |
