I've seen enough filter O-rings sticking to the filter mount that I ALWAYS feel around the mount surface to make sure nothing's stuck on there before spinning on a new filter.
But even with nothing stuck to the mount surface before you spin a new filter on, it's getting easier to over-tighten a filter these days, and if the gasket sticks to the mount before you stop tightening the canister, it can make the gasket/O-ring 'pooch' out as it ruptures and leak. And it might not happen immediately, either.
Always put some new oil on all of the mounting surface of the new filter's O-ring gasket, and once it gets seated to the mount I never go more than 1/2 turn beyond that.
Get rid of that 50 wt oil, too.....Especially in cooler weather, but you don't need it in the summer, either.