This is sort of depicted in AGE OF HEROES #3 out this week. I also don't want to spoil the events in DARKSTAR & THE WINTER GUARD #3, but generally, I think the Winter Guard would win, and here is why.
Ursa Major, while not the strongest, is an exceptional fighter. He is weak against fliers, but can stand toe to toe with the best of them. He literally fights like an animal.
Red Guardian is a powerhouse - and armed with his new Vibranium shield - he is pretty 'badass'.
Darkstar could dispatch the enemies quickly sending them straight into the Darkforce -- like the previous Darkstars did with Igor Drenkov. Remember, in the past, a Darkstar took down several of the X-Men by herself.
Crimson Dynamo is as well armed and has a level of military training that Iron Man does not. The Mark 14 armor that is depicted on the above cover is fairly powerful -- armed with deadly Dire Wraith technology.
Yes, Doc Spectrum, Speed Demon, and Hyperion are powerful, but they are also quite arrogant. Hyperion, in particular, has been shown to loss control in battle. I think they'll lose more out of a lack of strong teamwork. Hyperion would be better on his own.
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