[2] Bolsinger played in the Texas Collegiate League during the summer of 2007 and chose to transfer to the University of Arkansas for the 2008 season.

[7] Bolsinger began the 2010 season as the team's closer and earned a spot on the National Collegiate Baseball Writers Association "Stopper of the Year Watch List.

"[8] However, he made a successful transition to the starting rotation during the season[9] and earned Southeastern Conference pitcher of the week honors on May 10 when pitched eight innings and struck out 11 while allowing only two hits against the University of Mississippi.

[12] He spent most of 2011 with the Class-A South Bend Silver Hawks of the Midwest League, appearing in 32 games and starting 13 of them.

[12] Bolsinger began the 2013 season with nine appearances for Mobile, six of which were starts, and pitched to a 4–0 record, 2.51 ERA, and 31 strikeouts when he was promoted to Reno.

[16] Bolsinger was traded to the Los Angeles Dodgers in exchange for cash considerations on November 22, 2014.

[17] The Dodgers recalled him from the minors to make a spot start on April 23 against the San Francisco Giants.

[11] On August 1, 2016, the Dodgers traded Bolsinger to the Toronto Blue Jays for Jesse Chavez.

[26] He made his first appearance for the Blue Jays that night, making a start and allowing two runs in 52⁄3 innings in a 6–0 defeat to the Cleveland Indians.

Bolsinger would take the loss in the game after allowing a walk-off home run to Hanley Ramírez in the 15th inning.

[31] On December 13, 2017, Bolsinger signed with the Chiba Lotte Marines of Nippon Professional Baseball (NPB).

On March 16, 2021, Bolsinger signed with the Long Island Ducks of the Atlantic League of Professional Baseball.

[39] Bolsinger authored an opinion article in The Washington Post explaining his reason for suing the Astros.

[41] A refiling in Texas led to a subsequent nonfiling by August 2021, which meant the case was dismissed without prejudice.