In 2000, Bollinger, a redshirt freshman starter, assisted the Badgers in their second straight Rose Bowl victory along with teammate and Heisman Trophy winner Ron Dayne.

In one of the University of Wisconsin school papers, The Badger Herald, a full front-page article praised the quarterback as a "Triple Threat."

During his third year, the Badgers could not match the success of the two previous seasons as they posted a 5–7 overall record and did not earn a bowl game berth.

[3] Bollinger spent the entire year on the bench while Vinny Testaverde and Chad Pennington led the team as quarterbacks.

Bollinger did not play again until 2005, when first and second-string quarterbacks Chad Pennington and Jay Fiedler were both injured in a game against Jacksonville.

Bollinger was traded to the Minnesota Vikings in 2006 for defensive tackle C. J. Mosley and a draft pick where he was reunited with new head coach Brad Childress, his offensive coordinator in college.

[5] After a game against the Chicago Bears in which Vikings starting quarterback Brad Johnson threw 4 interceptions, Bollinger came in and replaced him.

After some shaky preseason and early season relief efforts in 2007, Bollinger was listed as the 3rd string quarterback on the Minnesota Vikings depth chart.

[6] While keeping a positive focus for his team, in early November 2007 Bollinger was ready once again to play his part in the role of the starting quarterback position for an NFL team after yet another series of unfortunate incidents of injuries and failed performances by 1st and 2nd string quarterbacks Tarvaris Jackson and veteran Kelly Holcomb.

[7] On September 8, 2008, Bollinger was signed by the Dallas Cowboys after the team waived wide receiver Mike Jefferson.

Bollinger was listed as the third string quarterback, backing up starter Tony Romo and his backup Brad Johnson.

After some failed performances by the veteran Brad Johnson, Bollinger made his first appearance for the Cowboys in the second half of the week 9 game against the New York Giants.

Though the Tuskers lost the championship, Bollinger was named season MVP through an online and text message vote by fans.

He would not play for the rest of the season as backup quarterback Chris Greisen took the Tuskers back to the UFL Championship, which they would later lose, once again to the Las Vegas Locomotives.