The Wings’ years of playoff disappointments were shorter though. Playoff streak started in 1992 and they won a series. By 1995 they were in the SCF, another conference final in 1996 then the Cup in 1997. And those regular seasons were great - #1 overall in 1995 and 1996. In contrast, this is the Leafs’ 9th straight year in the playoffs starting in 2017 and only have two first-round series wins to show for it. Their regular seasons have been good or very good but not great - two division titles, started on the road in the 1st round five of those nine years, never higher than #4 overall in the t regular season. I agree though about keeping Matthews and that they need to be less soft - Marchand would have helped.