Minnesota Wild

Roloson earned a roster spot with the Minnesota Wild in 2001. 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. Despite splitting goaltending duties with Fernandez, Roloson earned his first All-Star appearance at age 34, appearing in the 2004 NHL All-Star Game with the Western Conference team. He also won the Roger Crozier Saving Grace Award for having the NHL's best save percentage. During the 2004–05 NHL lockout, Roloson played for Lukko of the Finnish SM-liiga.

Edmonton Oilers

On March 8, 2006, Roloson was traded to the Edmonton Oilers in exchange for the first round pick that later became part of a trade for Pavol Demitra and a conditional draft pick that later became a third-rounder. Initially, Oilers general manager Kevin Lowe was harshly criticized for the acquisition when Roloson struggled during the regular season. Lowe was criticized both for not acquiring a better goaltender, and also for surrendering a first-round draft pick to a divisional rival.

Criticism was muted following sensational play by Roloson, backstopping the Oilers to the final of the 2006 playoffs. 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.

However, during Game 1 of the Stanley Cup Finals against the Carolina Hurricanes, Roloson suffered a third-degree MCL sprain of his right knee when Hurricanes forward Andrew Ladd was pushed into Roloson by a back-checking Oiler defenseman Marc-André Bergeron. Oilers head coach Craig MacTavish announced Roloson would not be able to continue in the series. It was also learned he had hyper-extended his right elbow in the collision as well. Back-up goaltender Ty Conklin replaced Roloson for the remainder of Game 1 and co-backup goalie Jussi Markkanen finished the series. The Oilers lost to the Hurricanes in seven games. Months of intense rehabilitation would follow in order to prepare Roloson for the 2006–07 season.

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.

In the 2007–08 season, Roloson started out strong before seeing his record fall to 7–12–0. By early January 2008, backup goaltender Mathieu Garon had taken the reins as starter. It was not until March 13, 2008, that Roloson saw regular play, coming in as relief for an injured Garon, starting each subsequent game.

When the 2008–09 season began, Roloson found himself vying for the starting goaltender position with Garon and upstart Jeff Deslauriers. For the beginning of the season, it appeared Garon was once again the starter but after some bad games Oiler head coach Craig MacTavish decided to rotate Garon, Deslauriers and Roloson by playing whoever had the hot hand. Eventually, the team traded Garon to the Pittsburgh Penguins and Roloson claimed the starting spot. Down the stretch, he started 36 consecutive games as the Oilers fought for a playoff spot. During this time, he became the oldest goaltender to start more than 60 games in a single season. Though the Oilers ultimately did not qualify for the playoffs, Roloson put up solid numbers, making upwards of 40 saves on a regular basis.

New York Islanders

On July 1, 2009, Roloson became an unrestricted free agent. After rejecting a one-year, $3 million offer from Edmonton, Roloson signed a two-year, $5 million contract with the New York Islanders. The Islanders also signed Martin Biron, who was to serve as Roloson's backup goaltender while Rick DiPietro was out on injured reserve. Roloson lost his first game as an Islander on October 3, 2009, in a shootout.

On November 23, 2009, Roloson made 58 saves on 61 shots in a 4–3 overtime win over the Toronto Maple Leafs. The 58 saves were a career high, and broke the Islander club record of 56, held by Rick DiPietro.^[2]

Tampa Bay Lightning

On January 1, 2011, Roloson was traded to the Tampa Bay Lightning in exchange for defenceman Ty Wishart.^[3] He won his first game with Tampa Bay in a 1–0 overtime shutout against the Washington Capitals. In his first 11 games with the Lightning, he recorded four shutouts. 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 and the Lightning ultimately advanced to the 2011 Eastern Conference Finals, where they were eliminated by the Boston Bruins in seven games. With his contract set to expire, the Lightning signed Roloson to a one-year, $3 million contract extension on June 29, 2011.^[4] He retired at season's end after the Lightning failed to qualify for the 2012 playoffs.