With morals on, i think Angel would figure out that these are good guys and he could avoid getting into heavy fighting long enough to convine the Winchesters he's on their side. They have held their hand when dealing with other monsters-turned good in the past.
Providing that nobody even tries to establish that they are all on the same side, then the odds should be good for an Angel victory.
Sam and Dean are both good hand to hand fighters but they are stuck at human-level and Angel has proven to be far above that, with aditional martial arts and fighting skills not demonstrated by the monsters of Supernatural.
Here's how i see the fight going down.
Winchesters should recognize Angel as a form of Vampire, though supernatural vamps look different than whedon vamps, so they would come to the fight with machete-style knives.
Angel is a long-time expert in melee weapons so disarming and or killing the Winchesters at this point would be a quick win. (Again, with Morals on, Angel would not go for the kill against a couple of human vigilante demon hunters)
Firearems have been shown to slow down Angel and other whedon vamps in the past, but the winchesters would have no knowledge of this and firearms prove generally useless against the monsters of supernatural, so i doubt they would bring them to this fight.
Of course, the colt would be a sure-fire win for the winchesters.
I don't think they can take Angel in a strait up fight. If they ambushed him, they could get the job done. They have shown good resiliance for humans, taking blows from all kinds of monsters and mysteriously never earning themselves a scar (haha), but they just don't have the physical stats to compete here. They need some kind of plot induced stat leveler to take a win.
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