2010-11: Roland McKeown skated for the Toronto Marlboros minor midget and bantam AAA teams. He played in seven games with the midget team at the OHL Cup and had 2 assists and 2 penalty minutes.
2011-12: McKeown was a captain for the Toronto Marlboros minor midget team and led the team's defensemen with 35 points in 28 regular season games. He scored 10 goals with 25 assists and had 30 penalty minutes. McKeown scored 3 goals with 7 assists for the Marlboros in seven games at the OHL Cup tournament. He was the second player taken in the 2012 OHL Priority Draft when he was drafted in the first round by Kingston.
2012-13: McKeown was named to the OHL's All-Rookie team, skating in 61 games for Kingston during the regular season and four playoff contests. He played for Team Canada in the 2013 U18 World Junior Championship and played for Canada Ontario in the 2013 U17 World Hockey Challenge. McKeown scored 7 goals with 22 assists and was -24 with 33 penalty minutes for the Frontenacs during the regular season. Kingston was third in the East Division despite a sub-.500 record and was swept by Barrie in a first round series. McKeown was -6 with 4 penalty minutes in the four-game series with the Colts.
2013-14: McKeown skated for Canada in the 2013 Ivan Hlinka Memorial Tournament before returning to Kingston for his second OHL season. In five games with Canada's gold medal-winning U18 team at the Ivan Hlinka tournament he had 1 assist and was an even plus/minus with 6 penalty minutes.