The WOBA instituted the Gold Award in 1991, as its Premier Award to recognize a Wolmer's Old Boy who has made significant positive contributions whether nationally or internationally.

The Awardees over the years are as follows:

  • 1991 The Most Hon, Sir Florizel Glasspole ON, GCMG, GCVO, - Governor General of Jamaica - 1973 - 1991
  • 1991 The Most Hon, Edward Phillip George Seaga, ON, PC - Prime Minister of Jamaica 1980 - 1989, Leader of the Opposition 1974 - 1980 & 1989 - 2006
  • 1992 Professor The Hon Hugh Hastings Wynter, OJ, CD JP - Head of Dept. of Ob/Gyn, former Dean Faculty of Medicine UWI
  • 1993 Senator The Hon Leacroft Robinson, OJ,QC,JP - Former Attorney General of Jamaica, President of the Court of Appeal, President of Commonwealth Caribbean Bar Association
  • 1994 Senator Douglas Orane, CD JP - Independent Senator & Chairman/CEO of Grace Kennedy & Company Limited
  • 1995 The Hon Patrick Rousseau OJ CD - President, West Indies Cricket Board & Managing Partner, Myers Fletcher & Gordon
  • 1996 Mr. Franz "Gerry" Alexander CD - Former Captain, West Indies Cricket Team
  • 1997 The Hon Allan Rae OJ CD - Former West Indies Cricketer, Jamaica Cricket Captain & West Indies Selector. Chairman Wolmer's Trust and Board of Management
  • 1998 Dr. Charles Royes CD - Department of Surgery, UHWI
  • 1999 Senator Col Trevor NN McMillan CD JP - Former Minister of National Security, Colonel Adjutant/Quartermaster - Jamaica Defence Force, Commissioner, Jamaica Constabulary Force
  • 2000 Mr. Ernest DeSouza CD JP, Spiritual Leader, Jewish Community
  • 2001 Mr. Lascelles Chin, CD JP - CEO of LASCO Group
  • 2002 Prof Patrick Bryan OD - Head of Dept. of History, UWI
  • 2003 Mr. Peter Jeffrey Dujon OD - Former West Indies Wicket Keeper
  • 2004 No award Wolmer's 275th
  • 2005 Mr. Ripton McPherson CD JP - Former Speaker of the House of Representatives 1972 - 1980
  • 2006 Mr. John Leslie "Jackie" Hendricks CD, Former West Indies Wicket Keeper, President - Jamaica Cricket Association
  • 2007 No award - Special Presentation to Outgoing Headmaster, Mr. Dave C. Myrie
  • 2008 Professor the Hon Gordon V. Shirley OJ, Pro Vice Chancellor & Principal, University of the West Indies, Mona Campus
  • 2009 Mr. Howard L. Hamilton CD JP, former Chairman, Caymanas Track Ltd, President Thoroughbred Owners & Breeders Association , former General Manager - Shell Company
  • 2010 - No Banquet
  • 2011 Mr. Milton Samuda - President, Jamaica Chamber of Commerce and Chairman, Wolmer's Trust
  • 2011 Professor Frederick Hickling CD - for Distinguished Career in Medicine and Psychaitry