Any bar that wants patrons during playoffs, especially now that The Habs have advanced, will want to have the game on. Otherwise they turn into ghost-bars. I'd pay attention to your locals to see who's smart enough to rent plasmas until June.
Café Diplomatico on College at Clinton (I think) has TVs on their patio. You'd maybe want to check if they're showing NHL/NBA, just in case (probably). I had a pretty good time watching World Cup 06 on that patio.