Boys have been playing rugby at Oakhill since 1955 and current players enjoy some of the best facilities in NSW, with Oakhill boasting four fields within the College campus.
Since joining the ISA competition in 1996, Oakhill 1st XV teams have won the ISA 1st XV Shield on six occasions. Age group teams have all enjoyed a lot of success with many teams going through their competitions undefeated. The ISA Rugby Championship Shield is awarded to the most successful school in all age divisions. Points are awarded on a weekly basis for both A’s and B’s teams culminating in the champion school. Oakhill has won the ISA Rugby Schools Championship Shield in 2007, 2009 (joint winner), 2010 and 2012.