Didn't mean to keep you waiting. I'm acutally going to change my answer for Round 3 to 50/50.
@the_magister said:
Round 1 - Pure hand to hand combat... BLOODLUST ON
May has better H2H feats than Widow does any way you slice it. She performed better against fodder (usually taking on more at a time than Widow has), has more fights against established characters, some of which have feats as good if not better than Widow, and even performed better against opponents with enhanced physicals. May even has the edge when it comes to statements as she was stated to have more black belts than Widow herself and was stated be the most lethal agent in SHIELD. Pretty cut and dry.
Round 2 - May gets a bo staff, Widow gets her tonfa...takes place in a dojo
Same as round one. Both don't really use those weapons often but have shown proficiency with them.
Round 3 - Natasha gets her Widow's Bite, May gets an ICER...start on opposite ends of a warehouse with standard body armor and no prep
Both May and Natasha are efficient and tactical shooters being able to tag their targets even in potions that would be considered too awkward or difficult to get an accurate shot off. Widow might have an edge due to almost shooting The Winter Soldier in the eye but I think May has shown that she's more than capable of holding her own in a (sort-of but not really) gunfight. Both May and Widow are masters at stealth so if they feel that things are getting too hot or they want to gain an advantage they could try to maneuver through the warehouse and get the drop on the other. So I think this ultimately is decided on their weapon of choice.
IMO Widow Bites are overrated. Ant-Man was fine after being hit by one directly, Rumlow was able to no-sell it due to nerve damage, and Widow herself was only down for a few seconds after hitting herself with it. And in Ant-Man's case he was KO'd by tasers in his solo, and Darren Cross was killed by a bug zapper before the electricity from the same bug zapper reanimated him. I don't really see Widow Bites as anything more than an advanced taser as anyone with a high tolerance to pain, or resisted the effects of electrical discharges shouldn't be downed by them or at the very least wouldn't be one shotted. That being said, May could fall to them as she was taken out by a taser early on in Season 2 (though she resisted electrical torture via live wires in the same episode so she might not go down easy). I'm not sure if the electricity from the wires was more powerful than the taser so I'm not sure if May could resist the Widow Bites.
ICERS on the other hand, are for all intents and purposes instant one-shots. Clothes and even body armor are not enough to prevent the dendrotoxin from entering the body. The only time an ICER round hasn't affected its target was when the target had an extremely higher metabolism/recovery rate than a normal human such as Centipede soldiers or are had release so much dopamine from the brain that it could resist it such as Hive-infected Inhumans. None of which applies to Natasha so if she gets tagged she's out for good.
It depends on who gets the first hit. I'd put money on May but I think I'm a little biased against Widow at times so I'm calling it even.
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