He has previously played in Major League Baseball (MLB) for the San Diego Padres, Detroit Tigers, Boston Red Sox, and Chicago Cubs.

[5] Wingenter made his professional debut with the Arizona League Padres and was later promoted to the Tri-City Dust Devils; in 12 combined games between both teams, he posted a 1–2 record with a 7.23 ERA.

He pitched 2016 with the Fort Wayne TinCaps, Lake Elsinore Storm and San Antonio Missions, pitching to a 3–1 record, a 1.70 ERA and a 1.06 WHIP in 39 games, and 2017 with San Antonio[6] where he went 2–1 with a 2.45 ERA with 64 strikeouts in 47.2 innings (49 games),[7] earning Texas League All-Star honors.

[11] Wingenter did not make an appearance for the Reds organization and elected free agency following the season on November 10, 2022.

[12] On January 15, 2023, Wingenter signed a minor league contract with the Detroit Tigers organization that included an invitation to spring training camp.

On July 6, 2024, the Tigers traded Wingenter to the Boston Red Sox in exchange for minor league pitcher CJ Weins.

[21] On July 9, the Red Sox purchased Wingenter's contract, adding him to their active roster.

[22] Wingenter was sent down to the Triple-A Worcester Red Sox three days later after giving up three runs in one inning of work.