The 2025 post-season promises chaos, drama, and some unforgettable hockey games. If the Edmonton Oilers want to punch their ticket to a second straight Stanley Cup Final, there’s one towering obstacle they may need to overcome: the Winnipeg Jets.

The Jets humiliated Edmonton in their season opener back in October, handing the Oilers a crushing 6-0 defeat. That slow start spiralled into a 2-4-1 record for Edmonton in their first seven games, while the Jets came roaring out of the gates with a jaw-dropping 16-1-0 record. Now, as the post-season looms, the stage seems set for yet another chapter in this heated rivalry.

In this edition of Throwback Thursday, let’s revisit the fiery playoff history between these two teams. From the old-school grit of the World Hockey Association (WHA) to today’s NHL battles, the Oilers and Jets have always delivered high-stakes drama. Ready? Let’s dive into the unforgettable moments that have defined this rivalry.

Before Wayne Gretzky became the face of the Oilers, Edmonton was struggling. In their first WHA playoff matchup, the Jets crushed the Oilers in a merciless four-game sweep. Game 1 saw the Jets dismantle Edmonton 7-3 at Winnipeg Arena. Game 2? A heartbreaker for the Oilers, as Ulf Nilsson scored an overtime dagger to secure a 5-4 Jets win. The series moved to Edmonton, but the results didn’t change. Bobby Hull broke a 2-2 tie in Game 3, and the Jets obliterated the Oilers 7-2 in Game 4 to close it out. Winnipeg didn’t just win the series; they went on to dominate the Calgary Cowboys and Houston Aeros to claim the Avco Cup.

Fast forward three years and a teenage Wayne Gretzky, who was acquired in a game of backgammon, was lighting up the WHA. The Oilers clawed their way to the Avco Cup Final, but the Jets were still too much to handle. Despite flashes of brilliance from Gretzky, Winnipeg won the series in six games, capping it with a commanding 7-3 victory. The Jets earned another Avco Cup, but this series signalled the beginning of the Gretzky era, a warning shot for the hockey world.

When the WHA folded in 1979, the Oilers and Jets joined the NHL, kicking off a new chapter in their rivalry. Here’s how Edmonton systematically dismantled Winnipeg in the NHL playoffs year after year.

By 1983, Edmonton was a powerhouse, and Winnipeg was no match. The Oilers swept the Jets in three games, with Gretzky scoring four goals in Game 1 alone. The Oilers breezed through the series and made it to their first Stanley Cup Final, though they fell to the Islanders dynasty.

The following year, the Oilers faced the Jets again in the first round. It wasn’t even close. Edmonton annihilated Winnipeg 9-2 in Game 1 and completed the sweep with a 4-1 win in Game 3. This time, the Oilers didn’t stop. Edmonton captured their first Stanley Cup, cementing their place as the NHL’s next great dynasty.

The Jets made it to the second round in 1985, only to be steamrolled by Edmonton in four games. The Oilers outscored the Jets 22-11 in the series, with Gretzky, Paul Coffey, and Mark Messier leading the charge. The Oilers would go on to win their second Stanley Cup.

By 1987, this rivalry was becoming downright embarrassing for Winnipeg. The Oilers swept the Jets again, marking their fourth playoff sweep in five matchups. Glenn Anderson’s overtime heroics in Game 1 set the tone, and Edmonton cruised through the series en route to yet another Stanley Cup victory.

Post-Gretzky, the Oilers faced their toughest challenge from Winnipeg in the 1990 division semifinals. The Jets jumped out to a 3-1 series lead, delivering heartbreak after heartbreak to Edmonton in double overtime victories. But just when Winnipeg thought they had finally turned the tide, Edmonton roared back. The Oilers won three straight games, including a decisive 4-1 Game 7 victory. As always, Edmonton didn’t stop there, as they went on to win their fifth and most recent Stanley Cup.

After years of playoff futility, the Jets finally had their moment in the 2021 first round. Led by Connor Hellebuyck’s clutch goaltending, Winnipeg stunned the McDavid-led Oilers in a four-game sweep. Edmonton’s Game 3 collapse, blowing a 4-1 lead, was the exclamation point on a series no Oilers fan wants to remember.

It was sweet revenge for Winnipeg, decades in the making. After getting hammered by the Gretzky Oilers during the 1980s, the Jets packed up and moved to Arizona in 1996 and became the Coyotes. Winnipeg didn’t get a team again until 2011 when the Atlanta Thrashers moved north. The new version of the Jets beating Edmonton was like the beginning of a long-awaited era in Winnipeg.

Now, as the 2025 post-season approaches, the Oilers and Jets are barreling toward another epic collision. Edmonton, powered by Connor McDavid and Leon Draisaitl, has its sights set on redemption. Winnipeg, riding a wave of dominance, looks like a team on a mission. If these two meet in the playoffs, there’s no doubt it’s going to be incredible.

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