2008-09: Rob O'Gara played for the Midget U-16 Long Island Royals (Atlantic Youth Hockey League). In 17 games, he scored 1 goal with 4 assists while accumulating 16 PMs. O'Gara also played for the Royals in the prestigious Chowder Cup tournament and had 2 assists in five games with 16 PMs.
2009-10: O'Gara played 33 games for the Royals, scoring 8 goals with 17 assists with 48 PMs.
2010-11: O'Gara transferrred to Milton Academy in Massachusetts for his junior year and enjoyed a breakout season from both a personal and team standpoint. While a bit overshaddowed by high-flying offensive defensemen like Vancouver prospect Patrick McNally, also a Long Island native, O'Gara provided rock-solid, stay-at-home defensive play as Milton won its first-ever New England Prep League championship. In 30 games, O'Gara chipped in 2 goals with 7 assists and had 22 PMs. O'Gara committed to attending Yale in 2012-13 and was selected by the Bruins in the 5th round (151st overall) of the 2011 NHL Draft.
2011-12: O'Gara attended Bruins prospect over the summer and skated for the Massachusetts champion Junior Bruins U18 team before returning to Milton Academy for his senior season. He was named to the All Independent School League and All New England all star teams. In 24 games for Milton he scored 5 goals with 20 assists. The Mustangs slipped a bit after winning the New England Prep League championship the previous spring – finishing 9-15-3. O' Gara played lacrosse for Milton Academy in the spring.
One of the youngest players in the 2011 draft, O'Gara is a long-term prospect who should continue to develop as he adds size and strength to his already impressive frame. While not the offensive force of some of the other young players to come out of Long Island in recent years, O'Gara is a skilled defensive defenseman who has worked to improve his mobility and agility since enrolling at Milton. Though he hails from Long Island, O'Gara is a bit of a hometown pick for the Bruins, having played with the Greater Boston Junior Bruins pre-season elite team as well as playing at Milton. He has one year of prep school remaining before enrolling at Yale so he will have time to continue to mature and develop.
After attending the recent Bruins prospect camp, O'Gara will return to Milton Academy for his senior year before enrolling at Yale to begin his college hockey career in 2012-13. O'Gara is another of the Bruins prospects who have the size and mindset to play the Bruins style of in-your-face hockey. He should continue to improve as he continues to grow and competes for a Yale program that has developed into one of the stronger programs in the East. With the Bruins fairly deep on the backline coming off their Stanley Cup championship, O' Gara is the type of long-term project they can afford to ensure that there is depth in the future. Style compares to Eric Brewer.