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.
O’Regan is a very skilled player with tremendous upside. From a purely offensive perspective he might just be the best playmaker in the system. He has a good (not great) shot, very good puck skills, and can carry the rubber well at his top speeds. He plays well under pressure and he can thread passes in the collegiate leagues as well as most NHL centermen.
Size will always be an issue for the 5'9 centerman, but his electric style of play (not reckless) will lend itself nicely to the professional leagues in a year or two once he gets a bit stronger and a bit more defensively adept. If the undersized forward continues to develop at his pace he has the potential to become a top line talent.
O’Regan will return to Boston University as top dog in his sophomore season and looks poised to breakout and become a Hobey Baker finalist. After a very good World Junior evaluation camp, it seems almost like a guarantee that O’Regan will represent the United States at the 2014 World Junior Championships.