You know, I was thinking that Medea could have easily won that war. Actually, only three Servants pose a serious threat to her: EMIYA, Heracles, and Gilgamesh. If they hadn't been summoned, Medea would have obtained the Grail.
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The only servant from the Fifth Holy Grail War that Medea can't defeat was Heracles (Saber (Artoria) is also a bad match for her, (maybe even more than Heracles); however, she can take control of her with Rule Breaker). The reason she was in trouble with EMIYA was that she had underestimated him. If she takes him more seriously, she probably could win (I don't mean she wins a head-on fight).
By the way, Medea probably won in one of the bad endings when she "Allied with Shirou".
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I'm not sure Medea has any countermeasures against UBW.
That's why I said that "I don't mean she wins a head-on fight".
Although she can teleport herself, so maybe she could escape from Reality Marble like Unlimited Blade Works.
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Is it possible to escape from the Reality Marble? I always thought that if you get trapped in it, you can't get out until the magus cancels it. Although, Medea can teleport before it's activated. I don't think she would just stand there and watch while EMIYA chants the spell.
What do you think?