Titchfield High School located on Fort George St. (Titchfield Hill) Port Antonio, the stars of the east, alongside Munro College, Mannings School and Cornwall College is one of the 4 schools to contest the first D Cup campaign back in 1950. The School would go on to qualify for 3 finals losing all three by the odd goal ; 2-1 vs Munro College in 1964,1 nil vs Cornwall College and Frome technical in 1982 a d 2003 respectively.

The School has produced a number of national players at youth and senior level. Devor Orgil,the most capped such player captained the first ever Jamaica team to beat the USA (2007) at any level, a 3-2 victory in the national stadium in U17 WCQ.