After a successful campaign with the Dartmouth Subways in which he recorded 31 points in 35 games Ryan Penny, a native of Fall River, was selected by the Moncton Wildcats as a forward in the fourth round of the 2010 QMJHL Draft. At the time, he was one of only two 16-year-olds on the team, a position that head coach Danny Flynn said was not easy to be in. He stayed with the team for four seasons as part of its rebuilding plan, steadily improving his game until his final season in 2013-2014. During that season, Penny accumulated 27 points in 41 games with the Wildcats before finishing off his junior career with the Rouyn-Noranda Huskies.

After his junior career, Penny signed with the Binghamton Senators of the American Hockey League (AHL). In 24 games with the Senators, he totalled 5 points before finishing out the season in the East Coast Hockey League (ECHL) with the Evansville Iceman collecting 23 points in 33 games.