Expectations weren’t very high for the Edmonton Oilers coming into 2005-06 campaign – they looked like they were fairly average, but nothing special. At the beginning of the season, there definitely weren’t very many people who predicted that we would see the team compete for the Stanley Cup in June. At the beginning of the season, they were given +2500 (25 to 1) odds to win the Stanley Cup.

The Oilers started the season slow, but were able to get things together by New Year’s Eve, when they had a respectable record of 22-14-4. They went 19-14-9 the rest of the way and were able to sneak into the eighth and final playoff spot in the Western Conference.

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The Oilers had a decent amount of cap room to work with during the summer prior to the season, so they were able to bring in a couple of key pieces to help them make a playoff run. With their first big move of the summer, the Oilers traded Eric Brewer, Jeff Woywitka, and Doug Lynch to the St. Louis Blues for star defenceman Chris Pronger, who was a former Norris and Hart Trophy winner.

The Oilers signed Pronger to a five-year $31.25 million contract. Pronger was huge for the Oilers – he recorded 56 points in 80 games that season, and added another 21 points in 24 playoff games. Not long after playoffs concluded, Pronger left Edmonton after requesting a trade; many believe it was due to his wife not liking the city.

The Oilers then went onto trade Mike York to the New York Islanders for Michael Peca, a former two-time Selke Trophy winner. Peca registered 23 points in the regular season and added 11 more in 24 playoff games.

The Oilers’ goaltending duo of Ty Conklin and Jussi Markkanen wasn’t working out, and the team decided they needed to do something. So, at the trade deadline, Edmonton sent their 2006 first-round pick to the Minnesota Wild to take a gamble on Dwayne Roloson, who had a 6-17-1 record at the time. The gamble paid off, and Roloson was a major component in Edmonton’s Cinderella run that season, going on to record a 2.33 goals-against average and a .927 save percentage. Oilers fans will always ask themselves what life would be like if Roloson hadn’t gotten injured in Game 1 of the Stanley Cup Final.

Edmonton wasn’t done there. After acquiring Roloson, they made the decision to trade Marty Reasoner, Yan Stastny, and a second-round pick to Boston for Sergei Samsonov, who won the Calder Trophy as the league’s top rookie in 1997-98. In 19 regular-season games with the Oilers, he recorded five goals and 16 points. He added 15 points in 24 playoff games.

Round 1 – Wings Clipped

Edmonton barely managed to get themselves into the playoffs, finishing as the eighth seed, which meant that they would have to take on the first seed, who just happened to be the Detroit Red Wings. The Wings were fresh off one of the best regular seasons that the NHL has ever seen. They finished with a 58-16-8 record that season, which is tied for fifth all-time for most wins in a season. Their 124 points that season ranks sixth all-time. So, the Oilers knew that they had their work cut out for them.

Edmonton dropped Game 1 3-2 in double overtime, but they were able to bounce back in Game 2, winning by a score of 4-2. The series was tied heading back to Edmonton, a result that not many expected. Game 3 went to double overtime once again, only this time it was Edmonton’s turn to take home the win – Jarret Stoll was the hero for the Oilers that night. Detroit evened the series up with a 4-2 win in Game 4, but Edmonton won Game 5 3-2, and had the chance to close the series out in Edmonton.

I remember Game 6 better than the rest of the games during this playoff run because it was the first Oilers game that I had ever been to. I remember Rexall Place being so packed and loud with nearly 17,000 Oilers fans getting ready to watch their team win their first playoff series since 1998. Detroit was up 2-0 heading into the third period, and the only thing that was on their mind was keeping their lead and heading back to Detroit for a decisive Game 7. Edmonton had other plans, though – Fernando Pisani scored two quick goals to open up the third and tie the game.

Johan Franzen was able to reclaim the lead for Detroit, but it didn’t last long. Shortly after, Ales Hemsky tied the game. Then, with 1:06 remaining in the third period, Hemsky was able to find the back of the net yet again to give Edmonton their first lead of the game, and the eventual series-winning goal. We had just witnessed one of the biggest upsets in NHL history as the eighth-seeded Oilers eliminated the first seeded Red Wings. Game 6 was also the last NHL game of Steve Yzerman’s legendary career.

Round 2 – Sharks Caught

After defeating the Presidents’ Trophy winners in six games, the Oilers were set to take on the San Jose Sharks, who had finished fifth in the Western Conference and were fresh off a series against the Nashville Predators, which they easily won in five games. This Sharks team had a very elite offense led by Joe Thornton and Jonathan Cheechoo, who took home the Art Ross and “Rocket” Richard Trophies, respectively. This was going to be another difficult series for the Oilers.

This series started off with back-to-back 2-1 wins by the Sharks, but Edmonton was able to cut the series lead in half with a thrilling triple-overtime win in Game 3. Shawn Horcoff scored the game-winner, assisted by Ryan Smyth, who had left the game earlier after taking a Chris Pronger clearing attempt to the mouth. I’m sure that watching Horcoff win the game for the Oilers made Smyth forget about the three teeth that he had just lost.

Game 3 ended up being the turning point in the series as it was all Oilers from there. They won Games 4 and 5 by the score of 6-3, and were once again heading home to Edmonton with the chance to close the series out in Game 6. Peca and Horcoff each scored, while Roloson picked up his first shutout of the playoffs to help the Oilers advance to the Western Conference Final.

Round 3 – Ducks Hunted

Edmonton was back in the Conference Final for the first time since the 1991-92 season, only this time instead of facing off against Chris Chelios and the Chicago Blackhawks, they were taking on Teemu Selanne and the Mighty Ducks of Anaheim. Anaheim had already beaten the Calgary Flames in seven games and had swept the Colorado Avalanche in the second round – now, the Oilers were standing in the way of them becoming one step closer to winning their first Stanley Cup.

The Oilers lost Game 1 in both of their previous series, but this time they were able to come out on top in the opening game with a 3-1 win. They picked up right where they left off the following game and were able to beat the Ducks 3-1 once again. Edmonton was heading home with a 2-0 series lead. The Oilers willed their way past the Ducks again, winning Game 3 by a score of 5-4 and taking a commanding lead in the series.

Anaheim was able to beat the Oilers 6-3 in Game 4 to try and get themselves back in the series, but it didn’t matter – Edmonton went onto win the fifth and final game of the series, 2-1. The Ducks were sent home, while the Oilers geared up for the what came next – they were the first No. 8 seed to ever reach the Stanley Cup Final.

Round 4 – Couldn’t Handle the Storm

The Oilers were back in the Stanley Cup Final for the first time since 1990. They were taking on the Carolina Hurricanes with hopes of winning the sixth cup in franchise history. This was pretty unfamiliar territory for the Hurricanes – they had only appeared in the Final once before, when they were beaten in five games by Detroit in 2002.

Carolina finished second in the Eastern Conference and fourth in the league with 112 points that season, so this was going to be no easy task for the Oilers. The Hurricanes beat Montreal in six games in round one, then they moved onto the second round where they dismantled New Jersey in five games. They met up with the Buffalo Sabres in round three in a series that went the distance, but Carolina came out on top by beating the Sabres 4-2 in Game 7.

Ales Hemsky had just tied the first game of the series 4-4 with little over five minutes remaining – all signs were beginning to point towards overtime, but that’s when disaster struck. Carolina forward Andrew Ladd received a pass and began to drive the net; this is when Oilers defenceman Marc-Andre Bergeron rushed in to make a hit and separate Ladd from the puck. It stopped the scoring chance, but what happened next was much worse.

As a result of Bergeron’s hit, Ladd was sent flying into Roloson, who had been so hot for the Oilers all playoffs, injuring his knee on the play. Ty Conklin came in as relief for the injured Oilers netminder. Later, some miscommunication behind the Oilers net led to Rod Brind’Amour stealing the puck from Conklin and wrapping it around into the wide-open net for the eventual game-winner. It was announced shortly after the game that Roloson would not be returning to the ice during the series, and Edmonton was forced to recall Jussi Markkanen.

Roloson’s injury was a tough blow for the Oilers, but there was still a lot of hockey left to play. Edmonton was dominated in Game 2, losing 5-0. The series moved to Edmonton for Games 3 and 4 and the Oilers knew they had to get a win to get themselves back in the series. They did exactly that – with a 2-1 win, hope was back. Carolina didn’t let Oilers fans get too excited, though – with a 2-1 win in Game 4, they now had a commanding lead in the series.

With a 3-1 series lead and the chance to win the Stanley Cup on home ice, Carolina came ready to play, but the Oilers weren’t ready to sit back and watch the Hurricanes celebrate just yet. Fernando Pisani scored the shorthanded overtime winner as the Oilers beat the Hurricanes and were heading to Edmonton with a chance to tie the series up. Game 6 was all Oilers – they forced a Game 7 with a 4-0 win.

The day had finally come – June 19, 2006. Carolina was on the hunt for their first Stanley Cup in franchise history, while Edmonton was looking to be the first No. 8 seed to win the championship. Unfortunately, Carolina won the game, 3-1, and secured their first-ever Stanley Cup, breaking the hearts of Oilers fans. It was certainly a memorable run for the Oilers, to say the least. It is unfortunate that we’ll never get to know how the series would have unfolded had Roloson not gotten injured.

It’s been nearly 14 years since Edmonton went on this run, and the Oilers have only made the playoffs once since, when they were knocked out in the second round by Anaheim in 2017. But the future looks bright for the Oilers, so it wouldn’t come as a major shock to see them make a couple more of these runs in the near future.

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