MCU Cap wins every time. There is no chance that Evans Cap will lose but 1990 Cap won't simply get steamrolled. He is going get his ass totally kicked but makes himself look good while doing it since he has feats like:
Strength feats:
[list]
[*] Tore through his metal restraints strapped onto his wrists and ankles with zero effort, as if they were made of paper. For comparison, remember what Superman did to his handcuff in Man of Steel
[*] He actually dragged a military truck to use as a shield with the same effort we would take to drag a heavy table, with one hand too
[*] He managed to hold his grip on Red Skull's wrist long enough that the villain was forced to cut his own hand off to escape. And Red Skull had caught a shield throw from 1990s Cap easier than WS and then thrown it back with enough force to completely embed it into the concrete floor
[*] Easily caught a guy who fell several stories with one hand while hanging from a ledge with the other. This dislocated the other guy's shoulder but not Cap's
[*] After he was thawed from the ice as an ice block he managed to awaken and break free of the ice block by himself.
[*] KOd two mooks by throwing a table onto them
[*] Ripped off a chunk of metal from a machinery to use as a shield and then sent a mook flying through a glass wall with it
[*] The mundane oneshotting mooks
[*] Easily ran shield-first right through a barbed wire fence, composed of several criss-crossed wires
[*] Sent people flying several feet with shield bashes.
[*] Punched a henchman through a metal grid
[*] Punched an enemy soldier hard enough to send him flying onto another, KOing them both
[*] With no leverage (with no leverage means strapped onto a rocket) he managed to kick a hole in the armor plating of the rocket
[/list]
Shield throw feats:
[list]
[*] Sliced a handgun in half with a shield throw
[*] Thrown his shield hard enough to cut clean through the wooden supports of a watchtower and spin around back to him
[*] Thrown it with enough force to cut through metal barrels
[*] Collapsed a wall with a shield throw
[*] Threw his shield and embedded it onto a wall. It was meant for RS but he dodged it. Cap then pulled it out
[*] Stopped a speeding sports bike cold with a shield throw. Inertia most probably killed the poor mook who as a result of the sudden stop was sent flying several feet and through a door head-first
[*] Sent RS flying off a cliff with a shield throw which then killed Skull's daughter on the return swing, apparently decapitating her
[/list]
Speed, agility and reflex feats:
[list]
[*] Avoided gunfire like 2016 Deadpool did
[*] The usual blocking handgun and machine gun bullets with shield. He even managed to block bullets while rolling on the ground to move across a clearing
[*] Dodged point blank handgun fire
[*] Front-flipped over a hechman and a car
[*] Front-flipped over a chair throw at him by RS
[*] Back-flipped and cartwheeled several feet away faster than RS could get up from the floor
[*] Left a few speeding mountain bikes in the dust, even when running downhill or uphill. Even when one of the riders used a slope as a ramp Cap was still way ahead
[*] Casually outran a sprinting Sharon
[*] Avoided gunshots while riding a bicycle carrying Sharon
[/list]
Durability and endurance feats:
[list]
[*] Managed to function for quite some time after being shot point blank twice in the chest, one in the heart and one in the other side
[*] Survived a surgical procedure which would've killed normal people. And then forced himself up despite not having fully healed from it
[*] After he was thawed from the ice as an ice block he managed to awaken and break free of the ice block by himself. No treatment nothing, broke out and went outside into the snow. Then he walked across the Alaskan icecaps until he came to the forest area. Then he outran some speeding mountain bikes for quite some time, as in way ahead and then was shot in the shoulder but healed from it no problem. And he was barely tired from all this
[*] Got run over by a speeding sports bike but was completely unharmed
[*] Was shot in the thigh but healed it in seconds
[*] Took several hits from the super-strong Red Skull, even from his cybernetic arm
[*] While Sharon was completely out of breath from hiding underwater, Cap wasn't even breathing hard
[/list]
He would look much better if he had any h2h skills. Unfortunately he had to be deployed immediately after the procedure. Despite their similar stats, Red Skull dominated in the beginning of both of their fights due to his fighting skills. Cap only won due the fight due to his sheer determination