You can’t ignore the teams Hasek was on. And he almost pulled off the unthinkable in 99. Also beat Roy head to head when he was older on a similarly stacked team as well as in Olympic competition. He’s just a flat out better goalie. I hate to say this man. I did not like Hasek at all. Roy won us cups and I’d love to say he was better but I don’t see it.
And Roy wasn’t consistent. When he was on he was spectacular but there were times he was just flat out bad.
1. Hasek has a better record than Roy head to head. That's true - but that hardly means anything? We're talking about a sample of ~20 games in a ~20 year career. Goalie head to head matchups are fun to track as fans, but completely meaningless in actuality. If Fleury ends up much better than Price - will you use that as an argument that he's a better goalie, because he happened to be better head to head? It's meaningless. Pretty cool for the player's ego maybe, but that's about it.
2. Hasek had a great run in 1999. Not as good as Roy's playoffs in 1993. Possibly not as good as a few others, such as 1989, 1986, 2001, 1996....yeah Roy is a monster playoff performer. The only player in history who can go head to head with Gretzky for playoffs. You are seriously underrating him.
You can't just give Hasek the edge because he plays on a bad team. His performances have to match/be better too. Otherwise - is McDavid better than Crosby because he's on a worst team? Or - better than Gretzky?
Roy >> Hasek for playoffs. For peak/prime/career.
Hasek has the better regular season record though (though Roy is no slouch there either).
Bottom line - I think you are massively underrating Roy in some of your posts.