He originally made a verbal commitment to play for Boston College, but that arrangement fell through when Clendening continued to pursue his options in the Ontario Hockey League (OHL).

[7] After two seasons with the Terriers, posting nine goals and 59 points for a combined +19 in 77 games, Clendening chose to leave the program in favor of pursuing an NHL career.

[citation needed] On January 16, 2016, Clendening was included in yet another trade, being sent to the Anaheim Ducks alongside David Perron in exchange for Carl Hagelin.

[citation needed] On January 10, 2018, Clendening, alongside Anthony Duclair was traded to the Blackhawks in exchange for Richard Pánik and Laurent Dauphin, returning to Chicago for a second stint.

[citation needed] As a free agent from the Blackhawks, Clendening left to sign a one-year, two-way contract with the Columbus Blue Jackets on July 1, 2018.

[20] He began the 2018–19 season on the Blue Jackets opening night roster, featuring in 4 games before he was placed on waivers and reassigned to AHL affiliate, the Cleveland Monsters.

Leading the Monsters blueline in scoring, Clendening posted 4 goals and 37 points in 45 games, before he was recalled by Columbus to add depth for the playoffs.

He made his NHL playoff debut with the Blue Jackets, appearing in game 3 of the Eastern Conference Quarterfinals against the Tampa Bay Lightning.

He appeared in seven championship games, putting up two assists as Team USA defeated Russia 5–0 to win a dark horse gold medal.