2009-10: Ryan Rupert skated in four junior A games with the Greater Ontario Junior Hockey League's Lambton Shores Predators and was one of the top scorers for the Elgin Middlesex Chiefs minor midget AAA team. He had 2 assists and 12 penalty minutes in his brief time with the Predators. Skating alongside his twin brother Matt Rupert on the Chiefs, Ryan scored 22 goals with 27 assists and had 40 penalty minutes in 30 games. In 15 playoff games he scored 11 goals with 10 assists and had 22 penalty minutes. Ryan Ruppert was selected by London in the third round (49th overall) of the 2010 OHL Priority Draft.
2010-11: Both Ryan and Matt Rupert split the season between the OHL's London Knights and Lambton Shores in the GOJHL. In 39 regular season games with the Knights, Ryan Rupert scored 9 goals with 18 assists and was plus-two with 30 penalty minutes. He skated in all six playoff games during the Knights' series with Owen Sound and was minus-four with 2 goals and1 assist and had 6 penalty minutes. In 25 games with the Predators he scored 15 goals with 21 assists and had 107 penalty minutes.
2011-12: Rupert skated in 63 of 68 games for London in his first full OHL season – missing five games due to a suspension he received in November for a post-game altercation. Rupert displayed both playmaking ability and an edge to his game – finishing plus-10 with 17 goals and 31 assists and leading the Knights with 120 penalty minutes. The Knights finished first in the Midwest Division and reached the Memorial Cup after winning the OHL playoff title. In 19 OHL playoff games Rupert scored 9 goals with 6 assists and was plus-five with 31 penalty minutes. Rupert was the second-leading scorer for London in the Memorial Cup behind Nashville prospect Austin Watson. In four games he scored 2 goals with 1 assist and was an even plus/minus with 8 penalty minutes. London lost to Shawinigan, 2-1 in overtime, in the championship game. Not among the 210 North American skaters listed in Central Scouting's final rankings prior to the 2012 NHL Draft, Rupert was selected by Toronto in the sixth round (157th overall).
2012-13: Rupert came on late in his third OHL season with London after getting off to a slow start and suffering a separated shoulder in November. Once again playing alongside his twin brother Matt Rupert with the Knights, he finished the regular season with 11 goals and 35 assists in 54 games and was +17 with 75 penalty minutes. London finished first in the Midwest Division with the OHL's best record and won the playoff championship to reach the Memorial Cup. Rupert scored 11 goals in 21 playoff games, tied with Max Domi (Phoenix) for second behind Bo Horvat (Vancouver), who scored 14 goals for London. Rupert had 9 assists and was +9 with 12 penalty minutes. He scored 1 goal with 2 assists and was -5 with 6 penalty minutes in five Memorial Cup games.
A pitbull on skates, Rupert plays right on the line of fair play (often times crossing it). He is among the OHL’s top two-way players and is also an underrated offensive player. He is a strong player maker due to his ability to find players in open ice. His skating ability is roughly average, which will be an area that will require development over the next season.
Rupert will return to the London Knights for the 2013-14 season, with pro eligibility the year following.