2007-08: Chosen in the third round, 49th overall, of the 2008 OHL Priority Selection by the Mississauga St. Michael's Majors.
2008-09: Cramarossa played for the Markham Waxers of the OJHL. In 38 games, he scored 7 goals and added 3 assists for 10 points.
2009-10: In his OHL rookie season, Cramarossa played in 64 games for the Majors. He scored 6 goals and added 10 assists for 16 points while also adding 60 penalty minutes. In 14 playoff games, Cramarossa picked up 2 assists.
2010-11: In 59 games, Cramarossa scored 12 goals and added 20 assists for 32 points. He also tacked on 101 penalty minutes on the season.
2011-12: Cramarossa returned to Mississauga for his third season in the OHL after attending the Ducks' training camp and was obtained by the Belleville Bulls in a January 2012 trade with the Majors. Cramarossa skated in 15 games with the Majors prior to the trade – missing time due to injury and a 10-game suspension in November for a hit to the head. He scored 6 goals with 5 assists and was minus-two with 40 penalty minutes. In 29 games with the Bulls he scored 8 goals with 8 assists and was minus-10 with 43 penalty minutes. Belleville faced the Ottawa 67's in the first round of the playoffs after finishing second in the East Division. Cramarossa led the Bulls in points and penalty minutes in the six-game series – finishing plus-one with 2 goals, 2 assists and 18 penalty minutes.