The Castlereagh GSC  Glentoran 'Player of the Year' for 2018-19, as voted for by Glentoran supporters, is Robbie McDaid. The trophy was first awarded to Billy Neill in the 57-58 season and all the winners since then are listed below.

2019/20  Robbie McDaid

2018/19  Robbie McDaid

2017/18 Curtis Allen

2016/17 Curtis Allen

2015/16 Curtis Allen

2014/15 Jordan Stewart

2013/14 Elliott Morris

2012/13 Andy Waterworth

2011/12 Colin Nixon

2010/11 Colin Nixon

2009/10 Richard Clarke

2008/09 Shane McCabe

2007/08 Jason Hill

2006/07 Gary Hamilton

2005/06 Colin Nixon

2004/05 Mark Glendenning

2003/04 Paul Leeman

2002/03 Gary Smyth

2001/02 Chris Walker

2000/01 Tim McCann

1999/00 Stuart Elliott

1998/99 Rory Hamill

1997/98 Justin McBride

1996/97 Michael Smyth

1995/96 Glenn Little

1994/95 Michael Smyth

1993/94 Alan Paterson

1992/93 John Devine

1991/92 Raymond Morrison

1990/91 George Neill

1989/90 Gary Macartney

1988/89 Gary Macartney

1987/88 Alfie Stewart

1986/87 Billy Caskey

1985/86 Raymond Morrison

1984/85 Gerry Mullan

1983/84 Tom Connell

1982/83 Jim Cleary

1981/82 Johnny Jameson

1980/81 Gary Blackledge

1979/80 Rab McCreery

1978/79 Roy Walsh

1977/78 Billy Caskey

1976/77 Billy Caskey

1975/76 Warren Feeney

1974/75 John Hill

1973/74 Warren Feeney

1972/73 Roy Stewart

1970/72 Tony Macken

1970/71 Roy Coyle

1969/70 Tommy Morrow

1968/69 Tommy Morrow

1967/68 Billy McCullough

1966/67 Arthur Stewart

1965/66 Albert Finlay

1964/65 Albert Finlay

1963/64 Trevor Thompson

1962/63 Eamon Byrne

1961/62 Matt Crothers

1960/61 Jimmy Murdough

1959/60 Jimmy Murdough

1958/59 Walter Bruce

1957/58 Billy Neill