During his NHL career, Roloson played for the Calgary Flames, Buffalo Sabres, Minnesota Wild, Edmonton Oilers, New York Islanders and Tampa Bay Lightning.

A Hobey Baker Award nominee and National Collegiate Athletic Association All-American while tending goal for University of Massachusetts Lowell, Roloson went undrafted after graduating.

In the 2002–03 season, Roloson shared goaltending duties with Manny Fernandez as the Wild made their first ever appearance in the Stanley Cup playoffs, reaching the Western Conference Final.

Initially, Oilers general manager Kevin Lowe was harshly criticized for the acquisition when Roloson struggled during the regular season.

He had a record of 12–5 through the first three rounds, and along with Chris Pronger, was considered a front-runner for the Conn Smythe Trophy as playoff MVP if the Oilers were victorious in the finals.

Back-up goaltender Ty Conklin replaced Roloson for the remainder of Game 1 and co-backup goalie Jussi Markkanen finished the series.

Roloson could have tested the unrestricted free agency market in the summer of 2006 but opted to re-sign with the Oilers on July 1, 2006, on a three-year contract.

When the 2008–09 season began, Roloson found himself vying for the starting goaltender position with Garon and upstart Jeff Deslauriers.

Though the Oilers ultimately did not qualify for the playoffs, Roloson put up solid numbers, making upwards of 40 saves on a regular basis.

In April 2011, Roloson recorded a shutout in a first round playoff Game 7 against the Pittsburgh Penguins, making him the oldest goaltender to do so.

Roloson was a member of the Canadian 2007 IIHF World Championship team that won gold in a 4–2 win against Finland in Moscow.

[5] Following his retirement from ice hockey, Roloson was immediately hired as a consultant to the Anaheim Ducks' AHL affiliate, the Norfolk Admirals.

On November 2, 2014, he suited-up in an emergency role after Ducks goaltender John Gibson suffered a pre-game injury and could not play the game against the Colorado Avalanche.