2009-10: Kerby Rychel played for the Belle Tire U18 team in Michigan. In 55 games he scored 30 goals with 19 assists and had 58 penalty minutes. Belle Tire reached the USA Hockey national tournament – advancing to the quarterfinals. Rychel, the son of Windsor GM and former NHL forward Warren Rychel, was drafted by Barrie in the first round (21st overall) of the OHL Priority Selection.
2010-11: Rychel opened his first OHL season with Mississauga St. Michael's, who had obtained his right from Barrie in a summer trade, before eventually be acquired by Windsor in a trade deadline deal in January. In 30 games with the Majors he scored 2 goals with 6 assists and was plus-five with 47 penalty minutes. Playing on a veteran Windsor team coming off back-to-back OHL championships, Rychel scored 5 goals with 8 assists and was minus-one with 26 penalty minutes in 32 games. The Spitfires reached the playoff semifinals, falling to Owen Sound. Rychel scored 2 goals with 5 assists and was minus-four with 14 penalty minutes in 18 playoff games. Rychel won a gold medal playing for Canada Ontario at the 2011 U17 World Hockey Challenge. In five games he scored 2 goals with 2 assists.
2011-12: Rychel was the leading scorer for Windsor in his first full season with the Spitfires and played for Canada in the 2012 U18 World Junior Championship. In 68 games he scored 41 goals with 33 assists and was plus-three with 54 penalty minutes. Windsor, after losing several veterans, slipped to fourth in West Division and lost in the first round of the playoffs. Rychel scored 2 goals and was minus-three in the four-game series with Memorial Cup-bound London. Rychel scored 5 goals with 3 assists in seven games as Canada won a bronze medal at the 2012 U18 WJC.
2012-13: Rychel again led the Spitfires in scoring, finishing with 40 goals and 47 assists in 68 games, in an otherwise disappointing season. Windsor missed the OHL playoffs for just the second time in coach Bob Boughner's tenure. Rychel finished with a minus-21 plus/minus and his 94 penalty minutes were second-most for the Spitfires. He was ranked 17th amongst North American skaters in Central Scouting's final rankings prior to the 2013 NHL Draft.