2009-10: Dan O’Regan attended the USA Hockey Select 15 Festival before his sophomore season at Roxbury Latin School in Massachusetts. He scored 23 goals with 21 assists for Roxbury Latin in New England Prep School League play.
2010-11: O’Regan transferred to St. Sebastian’s School and played for the Cape Cod Whalers U18 midget team. He scored 25 goals with 25 assists as a junior with St. Sebastian’s. In 14 games with the Whalers, including four playoff games, he scored 10 goals with 9 assists and had 2 penalty minutes. He committed to playing college hockey at Boston University in 2013-14. O’Regan was drafted by Dubuque in the eighth round (118th overall) of the 2011 USHL Entry Draft.
2011-12: O’ Regan skated for Team USA at the 2011 U18 Ivan Hlinka Tournament and in the 2012 U18 World Junior Championship. O’Regan returned to Massachusetts following the Hlinka Tournament, skating for the Cape Cod Whalers U18 team and St. Sebastian’s School. He joined the NDTP U18 team following the high school season and played for the gold medal-winning US squad in the U18 WJC. In three games at the Ivan Hlinka tournament, he scored 1 goal with 2 assists and was plus-two with 2 penalty minutes. He scored 5 goals with 6 assists in eight games with Cape Cod. O’Regan scored 21 goals with 35 assists and had 8 penalty minutes in 27 games for St. Sebastian’s. In 14 games with the US NDTP he scored 4 goals with 6 assists. At the U18 WJC he scored 1 goal with 3 assists and was plus-six as the USA won the tournament for the third straight year. O’Regan was ranked 76th amongst North American skaters in Central Scouting’s final rankings prior to the 2012 NHL Draft.
2012-13: O’Regan was the leading scorer for Boston University as a freshman. A teammate of fellow Sharks’ prospect Matt Nieto, he scored 16 goals with 22 assists in 39 games and was +2 with 16 penalty minutes. The Terriers finished in a three-way tie for third in Hockey East in the regular season and reached the Hockey East championship game, falling 1-0, to regular season champion Massachusetts-Lowell. O’Regan was invited to USA Hockey’s U20 Evaluation camp in Lake Placid in August, 2013.
2013-14: O’Regan was the third-leading scorer for a Boston University team that struggled to score goals in its first season under coach David Quinn following the retirement of long-time coach Jack Parker. He scored 10 goals with 12 assists in 35 games as a sophomore and was -19 with 22 penalty minutes. The Terriers finished ninth in Hockey East and lost to Notre Dame in a first-round playoff game.
2014-15: O’Regan had a breakout season for Boston University as a junior as the Terriers reached the Frozen Four championship game. The third-leading scorer for the Terriers behind freshman Hobey Baker award winner Jack Eichel (Buffalo) and senior Evan Rodrigues, he scored 23 goals with 27 assists and was +40 with 26 penalty minutes in 41 games. The Terriers captured the Hockey East regular season and playoff titles, winning eight straight games to reach the Frozen Four championship game before falling to Hockey East rival Providence, 4-3.
O’Regan is an undersized but skilled offensive player who is among the better playmakers in the Sharks' system. He has an accurate if not overpowering shot, significant puck skills, and the ability to make control the puck at his top speeds. He plays well under pressure and can thread passes effectively. O'Regan's size will likely be an issue at the pro level but his electric though not reckless style reminds some of players like Tyler Johnson and former BC rival Johnny Gaudreau. He should continue getting stronger and become more defensively aware but his development to this point is encouraging.
O’Regan returns to Boston University for his senior year in 2015-16; skating for what looks to once again be a very good Terriers team. He flourished in his junior year at Boston University in the shadow of 2015 second overall draft pick Jack Eichel last season. While Eichel's absence will be felt there are several high profile recruits joining the program this year. O'Regan will likely not match his gaudy numbers of last season but his play this year should provide a glimpse to his pro potential. If he continues to develop he should receive an entry-level contract from the Sharks. His offensive skills suggest he can be top-six talent at the NHL level though he may need time in the AHL to adapt to the pro game.