Daredevil vs. Spiderman - Love both characters, but DD should be barely breathing by the end of an encounter with Spidey if he's lucky.
Deadpool vs. Daredevil - Never understood why people pick DD over 'Pool. DD has a high level of skill, higher than Wade's, but straight up, DD does not have the damage output to KO or outlast Wade in a random encounter. If I had to choose between a highly skilled peak human with a just a set of billyclubs and a slightly less skilled enhanced human with a wide variety of weapons including grenades, swords, knives, guns, etc. I'd back the enhanced human everytime.
Hulk vs. any street leveler - Those fights are never written in Hulk's favor.
Deathstroke vs. Any of the Bat family (excluding CC) - It always bugged me that Deathstroke can fight superhuman opponents without as much trouble as he does when he fights Nightwing or Batman. I do believe that Slade is not as skilled as Bruce, but his other abilities outweigh the skill gap and I believe Slade shouldn't have a problem mopping the floor with any of the Bat family.