15, 2018, Pickard, and fellow Marlies goaltender Garret Sparks, were awarded the Harry "Hap" Holmes Memorial Award. After Pickard helped the Marlies win their first Calder Cup, he signed a one-year $800,000 contract extension to stay with the organization. During the 2018–19 pre-season, Sparks was chosen to be the Maple Leafs' backup, forcing Pickard to be put on waivers on October 1, 2018. He was claimed the following day by the Philadelphia Flyers. On November 23, 2018, Pickard had the fourth shutout of his career and his first with the Philadelphia Flyers in a 4–0 victory over the New York Rangers in the Flyers' traditional Black Friday matinee. The following day, he surrendered four goals on six shots against the Toronto Maple Leafs, and was pulled from the net in favor of Anthony Stolarz about twelve minutes into the contest. He did not start another game with the Flyers. With a .863% save percentage and a poor 4.01 goals against average, Pickard was once again placed on waivers on November 28. The following day, the Arizona Coyotes claimed Pickard off waivers. Remaining with the Coyotes as the club's third choice goaltender, Pickard made six appearances for the club, unable to win a game. Detroit Red Wings As a free agent from Arizona, Pickard opted to sign a two-year, $1.5 million contract with the Detroit Red Wings on July 1, 2019, his fifth team in two years. After a strong pre-season showing, Pickard was still assigned to Detroit's affiliate, the Grand Rapids Griffins, with whom he played the majority of the campaign. He received the AHL Player of the Week honor for the week of January 5. He was recalled to the Red Wings on three separate occasions after goaltenders Jimmy Howard and Jonathan Bernier went down with minor injuries. Pickard appeared in three games for the Red Wings, going winless and allowing 15 goals with a 5.46 GAA. Pickard was returned to Grand Rapids to assist in their playoff push on January 23, 2020. Less than two months later, the season was indefinitely suspended due to the COVID-19 pandemic. On December 1, 2020, prior to the 2020–21 NHL season, Detroit loaned Pickard to the Vienna Capitals of the ICE Hockey League to condition following the eight month break. He had a 3–3 record before being recalled to Detroit on January 3, 2021. Pickard was waived following training camp for the