Kingston College defeated Cornwall College to gain the first lien on the Alumni Trophy. Camperdown is the only team to win the Alumni Trophy multiple times. They won in 2001, 2002 and 2009.
Interestingly, only a few teams have played in the prestigious finals on several occasions, they are; Evander Childs High, Charlie Smith High, Munroe College, Kingston College, Calabar High, Camperdown High and St. Andrew Technical.
The Tournament took a two-year hiatus between 2007 and 2008 due to field unavailability at Evander Childs HS. It was reintroduced in 2009 and played at Van Cortlandt Park Stadium under new and current Director Bobby "Tego" Austin (Jamaica College).
We were back at Evander Childs High School briefly for the 2010 and 2011 seasons. Due to ongoing problems to acquire permits for the Evander Childs High School venue, the tournament was in the wilderness until 2021, when it was revived, presented and hosted by the Griffin Football Club. The Competition was played over two days at the end of June, at Haffen Valley Park, Bronx, New York with a change in format to an 8-A-side tournament for players Over 40 Masters.
| Years | Winners. | Runners Up |
|---|---|---|
| 1996. | Kingston College. | Cornwall College |
| 1997. | Dinthill Technical. | Evander High School |
| 1998. | St. Andrew Technical. | Charlie Smith High |
| 1999. | Evander Childs High | - |
| 2000. | Charlie Smith | - |
| 2001. | Camperdown High | - |
| 2002. | Camperdown High | - |
| 2003. | No Tournament | - |
| 2004. | - | - |
| 2005. | St. Mary's High. | Evander High School |
| 2006. | Jamaica College. | St. Andrew Technical |
| 2007. | No Tournament | - |
| 2008. | No Tournament | - |
| 2009. | Camperdown High. | Kingston College |
| 2010. | Munroe College. | - |
| 2011. | Excelsior High. | Munroe College |
| 2012- 2020. | No Tournament | - |
| 2021. | Calabar High. | Kingston College |