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 the Toronto Maple Leafs 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.
2013-14: Rupert was the fourth-leading scorer for the OHL’s London Knights in his fourth season of junior hockey. Once again skating with twin brother Matt, he scored 21 goals with 52 assists and was +36 with 54 penalty minutes in 68 regular season games. London finished third in the Midwest Division, advancing to the second round in the OHL playoffs, and participated in the Memorial Cup as the host team. Rupert scored 3 goals with 7 assists and had an even plus/minus with 10 penalty minutes in nine OHL playoff games. In three games at the Memorial Cup he was -3 with 1 assist and no penalties. Rupert signed a three-year entry-level contract with Toronto in April 2014.
Rupert is a pitbull on skates who plays right on the line of fair play (often times crossing it). Despite a lack of prototypical power forward size and limited skating ability, he plays a hard two-way game and is an underrated offensive player. Rupert is a strong player maker due to his ability to find players in open ice.
Rupert has been dealt by the Toronto Maple Leafs to the Ottawa Senators in the deal that also sent Dion Phaneuf, Matt Frattin, Casey Bailey, and Cody Donaghey to Ottawa. Coming back to the Maple Leafs are Jared Cowen, Colin Greening, Milan Michalek, Tobias Lindberg, and a draft pick.