McCutcheon played minor ice hockey in Toronto, and went to the 1962 Quebec International Pee-Wee Hockey Tournament with the Toronto Shopsy's youth team. He was recruited to play at Cornell under Ned Harkness. In his junior season McCutcheon led his team in goals while the Big Red compiled the first (and thus far only) undefeated national championship in NCAA history. After graduating in 1971 McCutcheon embarked on a professional career. Despite going undrafted, McCutcheon was signed by the Detroit Red Wings. After scoring only 7 points in 45 games across three leagues in 1971-72 McCutcheon settled down with the Virginia Wings in the mid-1970s, eventually receiving a call-up to the parent club. While McCutcheon was a capable minor league player he couldn't adjust to the NHL level, recording only 4 points in 37 games over three seasons with the Wings. He spent the entire 1977-78 season in the CHL before heading overseas to finish his playing career with EC Graz.
