2007-08: Kenny Ryan joined the USA National Team Development Program in Ann Arbor, Michigan; skating in 49 games for the U17 team. He scored 10 goals with 13 assists and had 65 penalty minutes. Ryan committed to playing college hockey at Boston College in 2009-10.
2008-09: Ryan returned to Ann Arbor for a second year in the NTDP – skating for the U18 team and winning a gold medal with the USA squad at the 2009 U18 World Junior Championship. He scored 27 goals with 22 assists and had 50 penalty minutes in 60 games for the NDTP U18 team. Ryan provided secondary scoring for the gold medal winning USA at the U18 WJC; scoring 4 goals with 1 assist and finishing plus-2 in seven games. The USA was 6-1 in the tournament; avenging it's only loss with a win over Russia in the gold medal game. Ranked 56th amongst North American skaters in Central Scouting's final rankings, Ryan was selected by Toronto in the second round (50th overall).
2009-10: Ryan began the year at Boston College but left the team shortly before the regular season started to play for the OHL's Windsor Spitfires. Skating for a powerful Windsor team that would win its second straight Memorial Cup, he scored 14 goals with 21 assists and was plus-nine with 33 penalty minutes in 52 regular season games. The Spitfires also won their second straight OHL championship and in 19 playoff games Ryan scored 3 goals with 2 assists and was minus-two with 14 penalty minutes. In four Memorial Cup games he was plus-three with 2 goals and 2 assists.
2010-11: Ryan returned to Windsor for a second season after attending camp with the Maple Leafs. Ryan was a solid, two-way, energy player for the Spitfires and scored at nearly a point-per-game clip during the regular season. He scored 22 goals with 38 assists and was plus-16 with 42 penalty minutes in 63 games. Windsor reached the West Conference finals after finishing second in their division. Ryan scored 4 goals with 8 assists and was minus-five with 25 penalty minutes in 18 playoff games. He signed a three-year, entry-level contract with Toronto in May 2011.
2011-12: Ryan made the jump from junior to pro hockey as a 20-year old – splitting the year between the AHL's Toronto Marlies and Reading in the ECHL. The youngest player on the Marlies, he was in and out of Toronto's lineup early in the year and also had a nagging injury. In 16 AHL games he scored 1 goal and was an even plus/minus with 9 penalty minutes. Ryan played a prominent role while with the ECHL's Royals; scoring 13 goals with 10 assists and finishing plus-one in 32 regular season games. In the Royals' five-game playoff series with Elmira he scored 3 goals with 2 assists and was minus-two with 27 penalty minutes.
2012-13: Ryan skated in 59 AHL games with the Toronto Marlies in his second pro season. He scored 9 goals with 12 assists and was +3 with 38 penalty minutes. Toronto finished first in the North Division and reached the second round in the AHL playoffs. Ryan played in all nine playoff games, finishing with an even plus/minus and no points with 13 penalty minutes.
A defensively savvy forward with great work ethic, Ryan is capable of playing both wing and center. He’s strong on his skates due to a stocky build and is tenacious on the forecheck. Offensively, he is able to chip in occasionally, but it is not an area of strength in his game.
Ryan made good strides in 2012-13 with the Toronto Marlies, and is scheduled to return to the tema for the 2013-14 season.