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On July 31, 2019, Winkler was traded to the San Francisco Giants along with Tristan Beck in exchange for Mark Melancon. He was designated for assignment the next day. He became a free agent after the season.

On December 6, 2019, Winkler signed a split major league contract worth $750,000 with the Chicago Cubs.

Winkler fractured his elbow on April 10, 2016, while facing the St. Louis Cardinals outfielder Randal Grichuk. He missed the remainder of the 2016 season, and as a result, resolved to adjust his mechanics to lessen stress on his elbow. Winkler was reactivated in August 2017, but due to injury had not yet fulfilled the major league service time requirement mandated of Rule 5 draftees. In January 2018, the Braves signed Winkler to a one-year contract worth $610,000. For the 2018 season, Winkler posted an ERA of 3.43 in 69 games. He struck out 69 in ​60  ⁄3 innings.

On December 11, 2014, the Atlanta Braves selected Winkler during the Rule 5 Draft. He was activated from the disabled list in September 2015. Winkler debuted on September 21, striking out two of the three New York Mets batters he faced.

Winkler made his professional debut for the Casper Ghosts, going 4–3 in 12 starts with a 3.92 earned run average (ERA) and 65 strikeouts over ​57  ⁄3 innings. He spent the 2012 season with the Asheville Tourists. He started 25 games, going 11–10 with a 4.46 ERA and 136 strikeouts in ​145  ⁄3 innings. Winkler started the 2013 season with the Modesto Nuts. On June 25, 2013 he combined with two relievers to pitch a no-hitter. He was promoted to the Tulsa Drillers near the end of the season. Overall, he was 13–7 with a 2.98 ERA and 175 strikeouts in 157 innings. The 175 strikeouts led all minor league players. He returned to Tulsa to start the 2014 season. He underwent Tommy John surgery to repair the ulnar collateral ligament of the elbow in June 2014.

Winkler was then drafted by the Colorado Rockies in the 20th round of the 2011 Major League Baseball draft and signed.

Winkler attended St. Anthony High School in Effingham, Illinois. He then attended Parkland College and was drafted by the Chicago Cubs in the 43rd round of the 2010 Major League Baseball draft, but did not sign and instead transferred to the University of Central Florida (UCF). In 2011, his junior season, he went 3-4 with a 4.70 ERA in 18 games.

Daniel Allen Winkler (born February 2, 1990) is an American professional baseball pitcher for the Chicago Cubs of Major League Baseball (MLB). He has played in MLB for the Atlanta Braves.