In early March of 2006, the Edmonton Oilers sat in eighth place in the Western Conference with a 32-21-9 record for 73 points, only three ahead of the Mighty Ducks of Anaheim.
The 2005-06 Oilers had already made a sizeable trade just over a month before the trade deadline, acquiring defenceman Jaroslav Špaček from the Chicago Blackhawks for prospect Tony Salmelianen. They also later moved Marty Reasoner, Yan Stastny, and a 2006 second-round pick (who turned out to be Milan Lucic) to the Boston Bruins for Sergei Samsonov.
However, there was no bigger trade for what was to come than a deal with the Minnesota Wild on March 8. The Oilers traded a 2006 first-round pick and a 2007 conditional third-round pick to the Wild for veteran netminder Dwayne Roloson.

Edmonton Journal – March 9, 2006

The background

Up to this point, netminding for the Oilers had been subpar, to say the least.
The team had three goalies on their roster. Mike Morrison mainly served as the backup, posting an .884 save percentage and a 2.83 goals-against average in 21 games for a 10-4-2 record, but was waived after the Roloson trade. Ty Conklin played 17 games with a 7-5-1 record and an .880 save percentage, along with a 2.80 goals-against average. The main starter for the Oilers, Finnish goalie Jussi Markkanen, had started the lion’s share of the games, posting an .880 save percentage and a 3.13 goals-against average in 37 games, with a 15-12-6 record. He’ll play a part in this story later.
There were 20 games after the Roloson trade, with the Oilers producing a pedestrian 9-7-4 record. In his first three games with the Oilers, Roloson had an abysmal .859 save percentage and an 0-2-1 record, as the Oilers fell out of a playoff spot on the morning of Mar. 12. However, Roloson finished the season strong, as he had a .916 save percentage in his final 16 games, along with an 8-5-3 record.
The Oilers clinched a playoff spot on Apr. 13 thanks to a 2-1 victory over the Mighty Ducks of Anaheim, as well as Vancouver Canucks 5-3 loss to the San Jose Sharks. However, Edmonton’s 95 points had them in the eighth spot while the Colorado Avalanche had the tiebreaker thanks to wins. 
Looming for the Oilers was a series with the Detroit Red Wings, who accumulated 124 points in the 2005-06 season. At the time, that was the fourth-highest point total in the season and remains the seventh-highest point total in a single season in history. How’d the Oilers fare? Well, they began one of the best postseason runs in sports history.

Detroit Red Wings

The Presidents’ Trophy curse is real. Only eight teams have won the Presidents’ Trophy and the Stanley Cup in the same season since it was awarded in the 1985-86 season. Interestingly, the Oilers won both in the first season of its existence, while the Detroit Red Wings were the most team to do so heading into the 2006 postseason, back in 2001-02.
However, a Presidents’ Trophy-winning team had only been knocked out in the first round twice in the 19-year history of the trophy. The 1990-91 Chicago Blackhawks fell to the Minnesota North Stars in six games, and the 1999-2000 St. Louis Blues fell in seven games to the San Jose Sharks. All of this is to say the Oilers were up against it.
Roloson was a big reason why the Oilers were able to become the third team in history to knock the regular season champions out in the first round. Roloson posted a .929 save percentage and a 2.50 goals-against average against the Red Wings.
In the opening game of the series, the Oilers fell in overtime, but Roloson saved 54 of 57 shots for a .947 save percentage. Game 2, a win, was just as impressive, as Roloson saved 33 of 35 shots for the 4-2 victory. In Game 3, Roloson had another 40+ save performance, saving 44 of 47 shots for a .936 save percentage, as Jarret Stoll scored in double overtime to lift the Oilers to a 2-1 series lead over the Red Wings.
Roloson’s only blemish came in Game 4, as he only saved 27 of 31 shots for an .871 save percentage in what was a 4-2 loss to make the series a best of three with it heading back to Detroit. The Oilers won an incredibly important Game 5 by a score of 3-2, with Roloson saving 30 of 32 shots, with one of those goals coming with 22 seconds left in the game.
Game 6 ended up being the decisive game, and Roloson had his second-worst performance, saving 33 of 36 shots. The Red Wings took a 2-0 lead into the third period, with Fernando Pisani tying the game with two goals in less than four minutes. Red Wings forward Johan Franzén scored midway through the third period to take the lead, only for Aleš Hemský to tie the game six minutes later with less than four minutes in the game.
And then, one of the most iconic goals of the 21st century happened, as Hemský broke into the offensive zone, lost the puck, but found open space beside Manny Legace, burying the game-winning goal with a 1:06 left in the game.

San Jose Sharks

Next up were the San Jose Sharks, who were in the midst of a long period of contention. On Nov. 30, 2005, the Sharks acquired Joe Thornton from the Boston Bruins, my favourite player growing up. In the 58 regular season games after the trade, Thornton scored 20 goals and 92 points, winning the Art Ross Trophy and the Hart Memorial Trophy that season.
But just like the Detroit Red Wings, Thornton, and the San Jose Sharks ran into Dwayne Roloson and the miracle 2005-06 Edmonton Oilers. Funnily enough, this was the only time in history where all four lower-seeded teams in a conference made it to the second round.
Somehow, Roloson was even better in this series, as he had a .931 save percentage and a 1.81 goals-against average. Despite good numbers in Game 1 (28 saves on 30 shots for a .933 save percentage) and Game 2 (36 saves on 38 shots for a .947 save percentage), the Oilers found themselves heading back to Alberta down 2-0 in the series.
Roloson had a terrific performance in Game 3, a win that the Oilers really needed as they couldn’t afford to go down 3-0 in the series. Well, Roloson saved 32 of 34 shots while playing over 100 minutes in a game that lasted over five periods. Thankfully, Shawn Horcoff ended it early in the sixth period of the game. If it wasn’t for Roloson’s huge glove save in the second overtime, the Oilers would’ve been down 3-0 in the series.
The series belonged to the Oilers from there. In Game 4, Roloson had 22 saves on 25 shots for an .880 save percentage, but the Oilers scored six to win 6-3 so it didn’t matter. In the return to California, Roloson allowed three goals on 24 shots for an .875 save percentage, but once again, the Oilers scored six goals in a 6-3 victory, sending the series back to Alberta.
Roloson’s best game of the series game in the decisive Game 6, as the Oilers defeated the Sharks 2-0 to send them to their first Conference Final series since 1990, where they awaited the Mighty Ducks of Anaheim.

Mighty Ducks of Anaheim

Throughout the 2006 postseason, Roloson got better with each series. The Oilers faced the sixth-seeded Mighty Ducks of Anaheim in the Western Conference Finals, and Roloson once again stood on his head.
Game 1 saw him save 31 of 32 shots for a .969 save percentage in a 3-1 victory. It was the same score in Game 2, as Roloson’s 33 saves on 34 shots (.971 save percentage) gave the Oilers a huge 2-0 advantage with the series shifting to Edmonton. Game 3 saw Roloson save 34 of 38 shots for an .895 save percentage, but the Oilers were able to win 5-4 despite nearly blowing a 4-0 lead.
The only loss suffered by the Oilers came in Game 4 with the Ducks’ back against the wall. They pounded Roloson with 45 shots, with Roloson saving 40 of them in a 6-3 defeat. In the series-clinching game in Anaheim, Roloson saved 32 of 33 shots (.970 save percentage) in a 2-1 victory.

Carolina Hurricanes

It’s time to re-live some pain here. Roloson’s last postseason game until 2011 was in Game 1 of the Stanley Cup Finals against the Carolina Hurricanes. The netminder allowed four goals on 23 shots, but more worrisome was the injury sustained with just over six minutes left in regulation in a 4-4 game.
Roloson’s season ended right there, but the Oilers’ hopes didn’t. The Hurricanes scored with 32 seconds left in the game to take Game 1. Playing the “what if” game sucks, but what if the Oilers had dressed Jussi Markkanen instead of Ty Conklin?
Markkanen started Game 2 and played the rest of the series. The Oilers lost games two and four and went down 3-1 in the series, but clawed back to send the series back to Raleigh. The most memorable moment of this series for Oilers fans was Fernando Pisani’s overtime goal in Game 5 to send the series back to Alberta.
Sadly, the miracle playoff run fell short in Game 7, as the Oilers fell 3-1. Markkanen didn’t play poorly by any means, posting a .905 save percentage and a 2.17 goals-against average. In the final game of the Oilers’ season, he saved 24 of 26 shots, as the Oilers were unable to score the game-tying goal to make it 2-2, much like the 2024 postseason.
The 2005-06 Oilers were the first eighth-seeded team to make the Stanley Cup Finals, with the Los Angeles Kings winning the Stanley Cup from the eighth-seed in dominant fashion six years later. Still, what an incredible run it was for Roloson and the Oilers.

Loose ends

Roloson played three more seasons with the Oilers from the 2006-07 season until the 2008-09 season. The Oilers fell short of making the playoffs in all three seasons, failing to miss out on the 2008 postseason by just three points.
Roloson signed a two-year deal with the New York Islanders to begin the 2009-10 season. That year, he had a .907 save percentage and a 2.77 goals-against average. Now 40 years old, Roloson played 20 games with the Islanders in 2010-11, before being traded to the Tampa Bay Lightning on New Year’s Day, 2011.
The Lightning went on a deep postseason run that season, with Roloson posting a .924 save percentage and a 2.59 goals-against average in 17 games played. Unfortunately for Roloson, the Lightning fell in Game 7 of the Eastern Conference Finals to the eventual Stanley Cup champions, the Boston Bruins. This was despite Roloson’s best efforts, as he saved 37 of 38 shots in a 1-0 defeat.
Roloson played one more season in the National Hockey League in 2011-12, posting an .886 save percentage and a 3.66 goals-against average in 40 games with the Lightning. At the age of 42, Roloson retired, the last player born in the 1960s to do so. Well, he did back up an Anaheim Ducks game during the 2013-14 season.
Funnily enough, my favourite player growing up, Joe Thronton, was the final player born in the 1970s to retire (unless Jaromír Jágr returns). In the Oilers’ return to the postseason 11 seasons after their heartbreaking Game 7 defeat, the Connor McDavid-led team defeated the San Jose Sharks and Joe Thornton in the first round.
Now, you may be wondering what the Minnesota Wild got out of the trade. The first-round pick was traded to the Los Angeles Kings, along with future Oiler Patrick O’Sullivan, for Pavol Demitra. That pick, which landed as the 17th overall selection in the 2006 draft, was used to select Trevor Lewis, one of just nine players still playing from that draft class. Lewis went on to win two Stanley Cups with the Kings and is just six games shy of reaching 1,000 for his NHL career. 

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