2008-09: Guptill played for the Brampton Capitals of the OJAHL. In 49 games, he scored 30 goals and added 34 assists for 64 points. Guptill picked up 1 assist in 3 playoff games for the Capitals.
2009-10: Played split the season between the Brampton Capitals (OJAHL) and the Orangeville Crushers of the CCHL (Junior A). In 10 games for the Capitals, Guptill netted 6 goals and added 5 assists for 11 points. In 19 games for the Crushers, Guptill scored 13 goals and added 13 assists for 26 points. He registered a +11 rating for the season. In 2 playoff games for the Crushers, Guptill picked up 1 assist and was a -3.
2010-11: Guptill moved to the USHL’s Waterloo Black Hawks in 2010-11. In 43 games, he notched 13 goals, 12 assists and 25 points with a minus-13 rating. Guptill saw plenty of power play time and some time with his team shorthanded. He was part of a two very good special teams units. Had trouble stringing together very good games on a below average Waterloo team.
2011-12: Guptill was named the CCHA Rookie of the Year after scoring 16 goals with 17 assists in 41 games for the University of Michigan as a freshman. He was the Wolverines second-leading scorer behind New Jersey prospect David Wohlberg and was plus-14 with 48 penalty minutes. Michigan finished second in the CCHA and reached the conference tournament championship game against Western Michigan; earning an at-large bid to the NCAA tournament.
A big body that quickly impressed Michigan coach Red Berenson with his offensive ability. A terrific goal scorer that exudes offensive potential. He thinks on a high-level and can keep up with talented offensive minds. He goes to the front of the net well and can score on the rush with a quality wrister. A good skater that protects the puck well. Still learning the game and his defensive responsibilities. He has a very projectable frame and could grow into a rather powerful forward down the line.
Is expected to be a mainstay in the University of Michigan offense.