Surprisingly, not that many. The Oilers made it to the cup final, losing to Carolina in seven games in the 05-06 season.
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The last time the Edmonton Oilers made the Stanley Cup Playoffs was in the 2005-2006 season when they made it to the Stanley Cup Finals. Since then, they have failed to make the playoffs.
Edmonton Oilers in 1984, 1985, 1987, 1988.
No, he did not win the Stanley Cup.
No, they did not win a Stanley Cup when Wayne Gretzky was on the team.
Bryan Trottier played on four straight Stanley Cup Championship squads in Long Island from 1980-1983, the team also played in the 1984 final but lost to the Edmonton Oilers
5 with the oilers but that's all i know.