He has previously played in the Chinese Professional Baseball League (CPBL) for the Fubon Guardians and Rakuten Monkeys.

In 2018, he was promoted to the major leagues by the New York Yankees, but he did not appear in a game, making him a phantom ballplayer.

[5] In 2011, Bollinger spent the year with the rookie ball Bristol White Sox, registering a 5-2 record and 4.23 ERA in 12 appearances.

In 2012, Bollinger again spent the year in rookie ball, this time for the Great Falls Voyagers, and pitched to a 4-3 record and 3.56 ERA in 17 games for the club.

Bollinger signed with the St. Paul Saints of the American Association of Independent Professional Baseball for the 2014 season.

Bollinger then signed with the Trois-Rivières Aigles of the Canadian American Association of Professional Baseball, and went 4-7 with a 4.73 ERA in 13 games for the team.

[8] On August 15, 2014, Bollinger was traded to the Winnipeg Goldeyes of the American Association of Independent Professional Baseball.

On November 26, 2018, Bollinger signed a minor-league contract with the San Diego Padres that included an invitation to spring training.

[23] On December 15, 2020, Bollinger signed with the Rakuten Monkeys of the Chinese Professional Baseball League for the 2021 season.