Preston is immensely capable at dealing with fodder, but has a great deal more difficulty with opponents who step outside the bounds of his rote mastery of statistical probabilities concerning return fire. Winter Soldier is a beast of an assassin that is legendary among even the likes of Black Widow, thus providing not only the skill necessary to at least compete with Preston on a level that makes Preston's rote mastery of the gun-kata useless, but also the physicals necessary to render at least some of Preston's most impressive melee feats useless or even dangerous (how often does Preston, in a fight against a near equal, grab/deflect enemy grabs? How well, realistically, will that work against someone not only capable of tanking melee hits from Cap, but with an arm capable of overpowering Cap's immense strength and with reflexes arguably capable of grabbing the deflecting arm?).
Preston's accuracy and capabilities in melee and gunplay are undeniable. Preston's track record against skilled opponents is less laudible and less decisive, especially when you consider his opponent displayed similar know-where-the-return-fire-might-come-from skills (deflecting bullets with his arm - and that's downplaying the possibility that WS is a bullet-timer, obviously) and physicals so far superior to any opponent Preston has faced as to make his opponents appear to be weak children in comparison.
Preston is a badass, no doubt, but he's best known for making meat out of fodder. Winter Soldier is not only not fodder, but almost certainly a match in skill (if more intuitive than trained, in comparison to Father) and completely dominant in physicals.
I can't deny that Preston might win some, but I think Winter Soldier is sufficiently skilled enough to make Preston's feats against massed enemies mostly meaningless, and his physicals should allow him to close the gap and dominate the melee in ways that Preston can't match. Given default rules, they're 10 feet from each other, and (reviewing the OP, they're further than that. They also have cover, and that should work sufficiently to WS's advantage as to make minimal difference in outcome) Winter Soldier should be able to deflect/avoid quickly enough to make the match into a melee, which Winter Soldier should dominate through a combination of his incredible hand-to-hand skills and his vastly superior physical stats.
7/10 Winter Soldier.
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