Kittredge posted a 2.25 ERA over 8 games in 2020. He sprained his UCL while pitching against the Boston Red Sox on August 12, 2020, which ended his season. On October 30, Kittredge was outrighted off of the 40-man roster and elected free agency. On December 8, Kittredge re-signed with the Rays organization on a minor league contract. On March 15, 2021, Kittredge triggered an opt-out clause in his deal and became a free agent, but re-signed with the Rays on a new minor league contract on March 20. On March 26, Kittredge was selected to the 40-man roster.
