In August 2020, Kennedy joined then 2. Bundesliga side Jahn Regensburg on a three-year contract.[4] He made his debut on October 31 against SC Paderborn. Kennedy's performances in his first season impressed, particularly in the 2020–21 DFB-Pokal, during which Regensburg knocked out Bundesliga side 1. FC Köln to advance to the quarter-finals.[5]
Kennedy's third season was marked by club struggles and injury, including a shoulder injury that forced him out of Canada's team for the 2022 FIFA World Cup.[6] At the end of the season Jahn Regensburg was relegated to the 3. Liga,[7] and Kennedy departed the club upon the expiration of his contract.[8]
While with Regensburg, Kennedy began to get interest in representing Canada internationally.[10] On 26 May 2021, Jahn Regensburg confirmed Kennedy had been called up to Canada for their upcoming 2022 FIFA World Cup qualification matches.[11] He made his debut for Canada on 8 June in the match against Suriname, playing the full 90 minutes in a 4–0 victory.[12] On 1 July, he was named to the final squad of the 2021 CONCACAF Gold Cup, but was replaced 9 days later by Frank Sturing for medical reasons.[13]
In late October 2022, Kennedy suffered a shoulder injury in a league match that his coach Mersad Selimbegovic confirmed would sideline him for "a few months," ruling him out of consideration for the 2022 FIFA World Cup squad.[14]
In June 2023, Kennedy was called-up to the final 23-man squad contesting the 2023 CONCACAF Nations League Finals.[15] On 19 June, he was called-up to the final squad for the 2023 CONCACAF Gold Cup.[16] On 9 July, during Canada's Quarter-final match against the United States, Kennedy would score an own-goal leading to a 2-2 draw. Canada would then lose 2–3 during the subsequent penalty shootout, eliminating them from the tournament.[17]
Personal life
Kennedy is of German descent through his mother, and holds dual Canadian-German citizenship.[18]