O'Boyle was born in Dublin and raised in Newbridge, County Kildare. O'Boyle also spent time living in the middle east while growing up where his father and former Irish Defence Forces Chief of Staff Conor O'Boyle was stationed at the time.
He attended Patrician Secondary School in Newbridge, Co. Kildare and Trinity-Pawling School in New York.
In a game for Ireland against Luxembourg in 2009, he scored six consecutive first half three-pointers and ended the game with 23 points in a winning effort. While at Trinity-Pawling School, O'Boyle was named first-team all-TriState and first-team all-New England. After graduating from Trinity-Pawling, O'Boyle accepted a scholarship to play at New Jersey Institute of Technology (NJIT).
In 2005, O'Boyle moved back to Ireland and joined UCD Marian for the 2005–06 Superleague season. During the 2006–07 and 2007–08 Superleague seasons, playing for Shamrock Rovers Hoops, O'Boyle led all Irish players in scoring and three-point shots made. O'Boyle transferred to the Ulster Elks in 2008 where he played for two seasons while completing postgraduate study.
In 2010–11, he appeared in just five games for Neptune Cork before leaving in December 2010. In the 2007 intervaristy final, O'Boyle led UCD to victory with a 39-point performance over Cork Institute of Technology. O'Boyle moved to New Zealand in early 2011 to work at Massey University as a lecturer in sport and recreation management.
While there, he played for the Manawatu Jets of the New Zealand NBL during the 2011 and 2012 pre-seasons. In 2013, O'Boyle moved to South Australia to work at the University of South Australia and to play for the Norwood Flames of the Central ABL. In 2014, O'Boyle was second in the league in three-point shots made while shooting 40% from the field.
He was awarded Irish Junior National Player of the Year in 2003. As a freshman, in the home opener for NJIT, O'Boyle led the team in scoring with 16 points to secure a win over the Division II number one ranked team in the nation, Philadelphia University coached by Basketball Hall of Fame coach Herb Magee, who labelled O'Boyle as a phenomenal shooter after the victory. Throughout his time playing in Ireland, O'Boyle also won four college intervarsity national titles in a row, three with University College Dublin (UCD) as an undergraduate, and one with University of Ulster as a postgraduate. In 2015, O'Boyle led Norwood with 18 points in the decisive final regular season game against Central Districts that sealed the minor premiership, and the team subsequently went on to win the 2015 Premier League championship with an 81–73 grand final win over Sturt.
He previously played for various teams within the Irish Superleague competition and was a member of the Irish national basketball team.
