Cutting has been elected co-captain of the men's rowing team for the 2007-08 season, as he has been a part of Holy Cross Rowing since his freshman year. He was a member of the men's freshman boat that won a silver medal at the 2005 New England Championship. Cutting has since been a part of the men's varsity eight boat that won gold in the 2006 and 2007 Patriot Challenges, silver at the 2006 New England Championship and bronze at the 2006 ECAC National Invitational Championship. Cutting has also rowed with the varsity eight for the 2006 and 2007 Eastern Sprints Regatta, as well as the 2006 and 2007 IRA National Championships.