Well, yes and no and kind of.
Emotionally, definitely. I don't think the fanbase has a big library of Matthews memories in the playoffs that are too enjoyable. 9 years and a whole lot of nothing so he's at a deficit now.
In terms of Stanley Cup wins, it's hard to compare the old era of two round Stanley Cups in the Original Six because you were essentially champion having advanced to the conference finals.
In comparison to the post expansion greats, most of Sittler, Sundin, Gilmour and Clark only had 1-2 big runs that cemented their legacy. So he could theoretically go to the ECF the next 2 years and he's matched most of them. That said, I go back to my original point that he's dug such a big reputational deficit he would probably have to win a cup outright to erase a lot of the "growing pains."