[1] After his playing career ended, Shildt became a coach at West Charlotte High School where he helped bring the baseball team their first winning season in 20 years.

[4] In his second season, Johnson City posted a 42–24 win–loss record, and after defeating its two playoff opponents, won the Appalachian League championship.

[5] Among the players he helped improve during the season include Appalachian League's Pitcher of the Year Ryan Copeland, and batting average champion Phil Cerreto.

[5] After Johnson City's season ended, Shildt was invited to spend some time on the St. Louis Cardinals roster to gain experience.

Shildt guided Springfield to its first Texas League championship before being recognized as Baseball America's Team of the Year in 2012.

He then spent two seasons as the manager for the Memphis Redbirds of the Class AAA Pacific Coast League.

[citation needed] Shildt was again promoted in 2017, this time to the MLB team, as the quality control coach.

Bob Nightengale of USA Today tweeted on August 28, 2018, that the team would remove the interim tag from Shildt's title and name him the club's permanent manager, awarding him a three-year contract.

Following a 3–2 win over the Chicago Cubs on September 22, 2019, the Cardinals clinched a playoff berth for the first time in Shildt's career as manager, and the first for the team since 2015.

[13] The Cardinals reached the playoffs in a shortened 2020 Major League Baseball season, losing in the Wild Card series.

[22] On January 26, 2022, Shildt was hired by the San Diego Padres to serve in a player development role.

[23] He began the 2022 season as the Padres' interim third base coach after Matt Williams had hip surgery during spring training.

It was the longest winning streak in the NL since 1935, broke the Cardinals' franchise record set in 1935, and was the first time the team won even 10 games in a row since 2001.