Apparently, contrōversus comes from the preposition contrā- + versus. So why does it have "ō" instead of "ā"? I checked Lewis and Short, but it doesn't explain the development of this vowel. I also found that contrāversus does in fact exist, although it seems to have a different meaning.
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Just as we have both intrā and intrō, citrā/citrō, ultrā/ultrō, there used to be a form contrō, which has only survived in this word. De Vaan adduces an Oscan form contrud. Historically, the -ō forms are masc./neut. ablatives, the -ā forms are fem. ablatives.
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Interesting! But, I still find this a bit confusing: what nouns are these ablatives of? And is it known why the feminine form ended up being more commonly used? Wiktionary lists nouns that seem to correspond to some of them, but not all (exter, ulter, citer). Surprisingly to me, "exter" seems to have the stem "exter-" rather than "extr-." May 6, 2016 at 22:18
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1@sumelic They're ablatives of "comparatives" in *-tero-. Scare quotes because these aren't normal comparatives of adjectives, but have the older PIE function of specifying "one of a pair" (inner as opposed to outer, etc.). Presumably the feminine forms imply some understood feminine noun that is being modified -- pars, maybe?– TKRMay 7, 2016 at 0:22