[1] Dickson was signed as an undrafted free agent by the St. Louis Cardinals in 2006,[1] after attending Tusculum College.

In 2007, with Single-A Quad Cities, Dickson's statline included an 11–7 win–loss record, with one save, and a 3.50 earned run average (ERA), in 31 games pitched (23 as a starting pitcher), covering 144 innings.

[5] Dickson's contract was purchased by the Cardinals from Memphis on June 30, 2011, to fill the roster spot created by Ryan Franklin's release the previous day, and he was promoted to the major leagues for the first time.

[6] Dickson made his major league debut on July 2,[1] against the Tampa Bay Rays, pitching a perfect 1+2⁄3 innings in relief.

With the conclusion of the 2019 season — Dickson's seventh year with the NPB Buffaloes — he had an overall record of 49–55, with 18 saves, and a 3.26 ERA.

For the 2021 season, Dickson was unlikely to make it to Japan, as the Japanese government was not issuing new visas and his family could not accompany him.

[13] On June 14, 2021, Dickson signed a minor league contract with the St. Louis Cardinals organization and was assigned to the Triple-A Memphis Redbirds.

[18] On October 10, 2019, Dickson was selected to play with the United States national baseball team at the 2019 WBSC Premier12.