Wins  | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 3 | |  Dale Shearer (G) | 2002 | | - |
| 3 | | John Dolan (F) | 1981 | Dundee, GBR | - |
| 3 | | Aaron Robertson (F) | 1998 | Kirkcaldy, GBR | - |
| 3 | | Michael Ireland (F) | 1996 | Edinburgh, GBR | - |
| 2 | | Macauley Armstrong (F) | 2000 | | - |
| 2 | |  James DeMeo (F) | 2002 | Bedford, MA, USA | - |
| 2 | | Joe Durkacz (D) | 1996 | | - |
| 2 | | Sean Dyer (F) | 1995 | | - |
| 2 | | Ben Edmonds (F) | 1998 | Dundee, GBR | - |
| 2 | | Jamie Edmonds (D) | 2004 | | - |
| 2 | | Kyle Ferguson (F) | 2002 | Elgin, GBR | - |
| 2 | |  Jack Flynn (D) | 1996 | Camberley, GBR | - |
| 2 | | Jonathon Hogan (F) | 1988 | Aberdeen, GBR | - |
| 2 | | Bradley Huntington (F) | 2002 | | - |
| 2 | | Jack Hutton (F) | 2004 | | - |
| 2 | | Gary Kelly (F) | 2005 | Dundee, GBR | - |
| 2 | | Mark Laing (F) | 1985 | | - |
| 2 | | Jordan Leyden (F) | 1991 | Glasgow, GBR | - |
| 2 | | Calum MacEachran (D) | 1984 | Aberdeen, GBR | - |
| 2 | | Kyle MacPhail (F) | 1990 | | - |
| 2 | | Owen Michie (D) | 2000 | Aberdeen, GBR | - |
| 2 | | Alexander Newman (F) | 1992 | | - |
| 2 | | Joshua Purvis (F) | 1997 | Amble, GBR | - |
| 2 | | Toby Reynolds (D) | 2001 | | - |
| 2 | | Callum Smith (D) | 1992 | Aberdeen, GBR | - |
| S | | Award Winner | Born | Birthplace | Drafted By |
|---|
| 24-25 | | Dale Shearer (G) | 2002 | | - |
| 24-25 | | Euan Simpson (G) | 2000 | Kirkcaldy, GBR | - |
| 24-25 | | Andrew Henderson (D) | 1997 | Dundee, GBR | - |
| 24-25 | | Robbie Hill (D) | 1994 | Dundee, GBR | - |
| 24-25 | | Sam McCluskey (D) | 1990 | Dundee, GBR | - |
| 24-25 | | Cameron McGiffin (D) | 1996 | Bath, GBR | - |
| 24-25 | | Logan Murphy (D) | 2008 | Stirling, GBR | - |
| 24-25 | | Ross Paul (D) | 1993 | | - |
| 24-25 | | Drew Rumgay (D) | 2001 | Dundee, GBR | - |
| 24-25 | | Charlie Scott (D) | 2001 | | - |
| 24-25 | | Billy Baxter (D) | 1985 | Dundee, GBR | - |
| 24-25 | | John Gordon (F) | 1995 | Dundee, GBR | - |
| 24-25 | | Lewis McIntosh (F) | 1992 | Dundee, GBR | - |
| 24-25 | | Robbie Barnett (F) | 1998 | Dundee, GBR | - |
| 24-25 | | Jaydn Baxter (F) | 2008 | Dundee, GBR | - |
| 24-25 | |  Michal Beca (F) | 1985 | | - |
| 24-25 | | John Dolan (F) | 1981 | Dundee, GBR | - |
| 24-25 | | Jack Henderson (F) | 2002 | Dundee, GBR | - |
| 24-25 | | Lewis Neave (F) | 2006 | | - |
| 24-25 | | Rio Page (F) | 2004 | | - |
| 24-25 | | Harvey Topen (F) | 2003 | | - |
| 24-25 | | Ben Brown (F) | 2004 | Dundee, GBR | - |
| 24-25 | | Sean Beattie (F) | 1994 | Kirkcaldy, GBR | - |
| 24-25 | | Michael Ireland (F) | 1996 | Edinburgh, GBR | - |
| 24-25 | | Grant Reekie (F) | 1989 | Dundee, GBR | - |
| 23-24 | | Aaron Forsyth (G) | 2002 | Wishaw, GBR | - |
| 23-24 | | Dale Shearer (G) | 2002 | | - |
| 23-24 | | Rory Wood (G) | 2006 | Forres, GBR | - |
| 23-24 | | Joe Durkacz (D) | 1996 | | - |
| 23-24 | | Jamie Edmonds (D) | 2004 | | - |
| 23-24 | | Calum MacEachran (D) | 1984 | Aberdeen, GBR | - |
| 23-24 | | Owen Michie (D) | 2000 | Aberdeen, GBR | - |
| 23-24 | | Connor Nelson (D) | 2007 | Elgin, GBR | - |
| 23-24 | | Toby Reynolds (D) | 2001 | | - |
| 23-24 | | Callum Smith (D) | 1992 | Aberdeen, GBR | - |
| 23-24 | | Jamie Whitelaw (D) | 1992 | | - |
| 23-24 | | Jack Flynn (D) | 1996 | Camberley, GBR | - |
| 23-24 | | Ross Michie (D) | 2005 | | - |
| 23-24 | | Ben Edmonds (F) | 1998 | Dundee, GBR | - |
| 23-24 | |  Nils Tanner (F) | 2001 | Karlstad, SWE | - |
| 23-24 | | Macauley Armstrong (F) | 2000 | | - |
| 23-24 | | James DeMeo (F) | 2002 | Bedford, MA, USA | - |
| 23-24 | | John Dolan (F) | 1981 | Dundee, GBR | - |
| 23-24 | | Sean Dyer (F) | 1995 | | - |
| 23-24 | | Logan Gordon (F) | 2008 | | - |
| 23-24 | | Imran Harrell (F) | 2001 | | - |
| 23-24 | | Jonathon Hogan (F) | 1988 | Aberdeen, GBR | - |
| 23-24 | | Bradley Huntington (F) | 2002 | | - |
| 23-24 | | Jack Hutton (F) | 2004 | | - |
| 23-24 | | Mark Laing (F) | 1985 | | - |
| 23-24 | | Jordan Leyden (F) | 1991 | Glasgow, GBR | - |
| 23-24 | | Kyle MacPhail (F) | 1990 | | - |
| 23-24 | | Iain Malcolm (F) | 1991 | Dundee, GBR | - |
| 23-24 | | Alexander Newman (F) | 1992 | | - |
| 23-24 | | Joshua Purvis (F) | 1997 | Amble, GBR | - |
| 23-24 | |  Brant Saretsky (F) | 1996 | Wainwright, AB, CAN | - |
| 23-24 | | Kyle Ferguson (F) | 2002 | Elgin, GBR | - |
| 23-24 | | Gary Kelly (F) | 2005 | Dundee, GBR | - |
| 22-23 | | Dale Shearer (G) | 2002 | | - |
| 22-23 | | Rory Wood (G) | 2006 | Forres, GBR | - |
| 22-23 | | Joe Durkacz (D) | 1996 | | - |
| 22-23 | | Jamie Edmonds (D) | 2004 | | - |
| 22-23 | | John Paul Jack (D) | 1999 | Inverness, GBR | - |
| 22-23 | | Calum MacEachran (D) | 1984 | Aberdeen, GBR | - |
| 22-23 | | Owen Michie (D) | 2000 | Aberdeen, GBR | - |
| 22-23 | | Toby Reynolds (D) | 2001 | | - |
| 22-23 | | Callum Smith (D) | 1992 | Aberdeen, GBR | - |
| 22-23 | | Euan Smith (D) | 1999 | | - |
| 22-23 | | Jack Flynn (D) | 1996 | Camberley, GBR | - |
| 22-23 | | Ben Edmonds (F) | 1998 | Dundee, GBR | - |
| 22-23 | | Nils Tanner (F) | 2001 | Karlstad, SWE | - |
| 22-23 | | Macauley Armstrong (F) | 2000 | | - |
| 22-23 | | James DeMeo (F) | 2002 | Bedford, MA, USA | - |
| 22-23 | | Jack Durkacz (F) | 1998 | Elgin, GBR | - |
| 22-23 | | Sean Dyer (F) | 1995 | | - |
| 22-23 | | Jonathon Hogan (F) | 1988 | Aberdeen, GBR | - |
| 22-23 | | Bradley Huntington (F) | 2002 | | - |
| 22-23 | | Jack Hutton (F) | 2004 | | - |
| 22-23 | | Tom Johnston (F) | 1995 | | - |
| 22-23 | | Mark Laing (F) | 1985 | | - |
| 22-23 | | Sean Ledgard (F) | 2000 | | - |
| 22-23 | | Jordan Leyden (F) | 1991 | Glasgow, GBR | - |
| 22-23 | | Kyle MacPhail (F) | 1990 | | - |
| 22-23 | | Alexander Newman (F) | 1992 | | - |
| 22-23 | | Joshua Purvis (F) | 1997 | Amble, GBR | - |
| 22-23 | | Kyle Ferguson (F) | 2002 | Elgin, GBR | - |
| 22-23 | | Gary Kelly (F) | 2005 | Dundee, GBR | - |
| 21-22 | | Craig Chalmers (G) | 1994 | Kirkcaldy, GBR | - |
| 21-22 | | Ben Keddie (G) | 2004 | Kirkcaldy, GBR | - |
| 21-22 | | Jamie Chandler (D) | 1996 | Slough, GBR | - |
| 21-22 | | Reece Cochrane (D) | 2001 | Kirkcaldy, GBR | - |
| 21-22 | | Liam Danskin (D) | 2000 | Kirkcaldy, GBR | - |
| 21-22 | | Kyle Horne (D) | 1980 | Kirkcaldy, GBR | - |
| 21-22 | | Steven MacDonald (D) | 1985 | Kirkcaldy, GBR | - |
| 21-22 | | Ali McLeod (D) | 2004 | Kirkcaldy, GBR | - |
| 21-22 | | Thomas Muir (D) | 1986 | Kirkcaldy, GBR | - |
| 21-22 | | Joshua Saunders (D) | 2006 | Edinburgh, GBR | - |
| 21-22 | | Gregor Smith (D) | 1997 | Kirkcaldy, GBR | - |
| 21-22 | | Cameron Wilkie (D) | 2006 | Kirkcaldy, GBR | - |
| 21-22 | | Allan Anderson (F) | 1989 | Kirkcaldy, GBR | - |
| Wins | | Award Winner | Born | Birthplace |
|---|
| 3 | | Steven Wishart | 1979 | Kirkcaldy, GBR |
| 2 | | Rab Brown | 1963 | Dundee, GBR |
| 2 | | Jordan Leyden | 1991 | Glasgow, GBR |
| 2 | | Fraser MacEachran | 1981 | Dumbarton, GBR |
| 2 | | Ian Turley | 1986 | |
| 1 | | Jeff Hutchins | 1978 | Toronto, ON, CAN |
| 1 | | Barry Carnegie | 1980 | Dundee, GBR |
| 1 | | Kyle Horne | 1980 | Kirkcaldy, GBR |
| 1 | | Steven King | 1975 | Kirkcaldy, GBR |
| 1 | | Lewis Leslie | 1999 | Perth, GBR |
| 1 | | Cameron Wilson | 2004 | Kirkcaldy, GBR |
| 1 | | Martin Grubb | 1976 | Kirkcaldy, GBR |
| 1 | | Rab Murray | - | |
| 1 | | Jamie Thomson | 1977 | Dumfries, GBR |
| 1 | |  Martin Cingel | 1976 | Povazska Bystrica, SVK |
| 1 | | Grant Deans | - | |
| 1 | | Martin Gill | - | |
| 1 | | Tony Hand | 1967 | Edinburgh, GBR |
| 1 | | Jock Hay | 1954 | |
| 1 | | John Dolan | 1981 | Dundee, GBR |
| 1 | | Craig Evans | - | |
| 1 | | John Gordon | 1969 | |
| 1 | | David Smith | 1973 | St. Andrews, GBR |
| S | | Award Winner | Born | Birthplace |
|---|
| 24-25 | | Rab Brown | 1963 | Dundee, GBR |
| 24-25 | | Jeff Hutchins | 1978 | Toronto, ON, CAN |
| 23-24 | | Barry Carnegie | 1980 | Dundee, GBR |
| 23-24 | | Jordan Leyden | 1991 | Glasgow, GBR |
| 23-24 | | Fraser MacEachran | 1981 | Dumbarton, GBR |
| 22-23 | | Jordan Leyden | 1991 | Glasgow, GBR |
| 22-23 | | Fraser MacEachran | 1981 | Dumbarton, GBR |
| 21-22 | | Kyle Horne | 1980 | Kirkcaldy, GBR |
| 21-22 | | Steven King | 1975 | Kirkcaldy, GBR |
| 21-22 | | Lewis Leslie | 1999 | Perth, GBR |
| 21-22 | | Cameron Wilson | 2004 | Kirkcaldy, GBR |
| 21-22 | | Steven Wishart | 1979 | Kirkcaldy, GBR |
| 19-20 | | Martin Grubb | 1976 | Kirkcaldy, GBR |
| 19-20 | | Rab Murray | - | |
| 19-20 | | Jamie Thomson | 1977 | Dumfries, GBR |
| 18-19 | | Martin Cingel | 1976 | Povazska Bystrica, SVK |
| 18-19 | | Grant Deans | - | |
| 18-19 | | Martin Gill | - | |
| 18-19 | | Tony Hand | 1967 | Edinburgh, GBR |
| 18-19 | | Jock Hay | 1954 | |
| 17-18 | | Rab Brown | 1963 | Dundee, GBR |
| 17-18 | | John Dolan | 1981 | Dundee, GBR |
| 17-18 | | Craig Evans | - | |
| 17-18 | | John Gordon | 1969 | |
| 16-17 | | Ian Turley | 1986 | |
| 15-16 | | Steven Wishart | 1979 | Kirkcaldy, GBR |
| 14-15 | | David Smith | 1973 | St. Andrews, GBR |
| 14-15 | | Steven Wishart | 1979 | Kirkcaldy, GBR |
| 12-13 | | Ian Turley | 1986 | |