I'm kind of torn on this one.
Daredevil vs Crossbones (Winter Soldier)
Rumlow was one of SHIELD/Hydra's best combatants. In Winter Soldier we saw him last longer than anyone else against Cap in the elevator fight, embarrass Sharon Carter even though she had him at gunpoint and thrash Falcon.
Daredevil's on another level though. We've seen him fight his way through entire criminal gangs and small armies of hand ninjas, often whilst injured. He's also beaten far tougher, more skilled opponents than Rumlow (Nobu, Kingpin, Punisher, Bullseye).
Daredevil wins.
Daredevil vs Crossbones (with his Civil War battle suit)
In Civil War, Crossbones came back with a new armour/exoskeleton suit that gave him the strength and durability to easily overwhelm Black Widow and to give Captain America a challenge. He also has damaged nerve endings that gave him extreme pain tolerance.
We've seen Daredevil briefly hold his own against an extremely skilled superhuman before (resurrected Elektra) and I'm sure he could put up a fight here too. Ultimately though, Crossbones has the power/skill to overwhelm him whereas Matt just doesn't hit hard enough to put down an enemy that tanked multiple hits from Captain America.
Crossbones wins.
Haven't seen him in a minute.....
