R1-Oliver Queen: I think Oliver will incur some semi-moderate damage but will win due to a speed and agility advantage and possibly skill as well.
R2-Bruce Wayne: It will be a hard fought battle but I think Batman has a significant durability advantage via his suit which will allow him to tank more of Olivers attacks and allow him to use less energy defending and make strategic attacks with high efficacy against Oliver and although Oliver may have a stamina advantage it will be damage that will wear him down and result in him losing.
Does he get the Iron Spider Suit? I would assume not as its capabilities go beyond the realm of a purely H2H match. Assuming this is the case then he loses for sure. There are too many for him to face but even with Captain America and Winter Soldier alone with morals off he would lose. If he gets to use his webs he will have a chance but it will be pretty difficult.
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