I think this is similar to your pair in that (a) they are real polar opposites and (b) not everyone will consider "ambitious" to be a negative characteristic. (cf. Shakespeare's Julius Caesar, where that's an issue.) Within the academic world, where the ideal is to be driven by pure love of learning and teaching and sharing in the building of new knowledge, "ambitious" is mostly considered a negative quality. In the business world I think it's positive. (A 19th century president of the University of Massachusetts, who established a sister-university relationship with Hokkaido University, is known and respected in Hokkaido for the advice, "Boys, be ambitious!". That was positive.)
But nowhere, including academia, is "unambitious" positive. So within my subculture, both are negative, and the positive alternative is to be working hard and well, but for "pure" motives, not for fame or money or power.

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Thanks, Barbara! In Russian, BTW, амбициозный is said to be moving towards positive (see Irina Levontina's essay in Stengazeta), but for me it still means something rather negative.

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Thanks, I'll look at that! And I just thought of another interesting pair: ladylike and unladylike. Ladylike used to be positive, but now it would be positive only in some circles and quite insulting in other, more feminist, circles. (Many (most?) adult females now prefer to be called 'women', and consider the term 'ladies' to be a bit condescending.) But not wanting to be called 'ladylike' doesn't mean wanting to be called 'unladylike'!

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And what about "gentelmanlike"? Is it still positive, or is it just completely non-existent?

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We need a sociolinguist who is keeping statistics over time to be sure -- but for myself, "gentlemanly" is positive but old-fashioned.

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Thanks. I guess "genltelmanlike" must have been refreshed by the overwhelming popularity of some Jane Austen's TV-adaptations...

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But how does working hard for "pure" motives differ from "unambtiuous". Does it mean that one's ambitions should be also somehow "pure"?

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And for me, actually, неамбициозный is definitely positive. I would freely apply this adjective to myself, and probably feel that I am not being modest enough.

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Well, reading Irina Levontina's article made me realize (yet again) that close cognates or even borrowings can have interestingly different shades of meaning in Russian and English. But since there are often differences within one language across subcultures on such evaluative words, I'm not even sure how representative my own intuitions about "unambitious" are. But I checked some quotations on a dictionary site (http://www.thefreelibrary.com/_/search/Search.aspx?By=0&SearchBy=4&Word=unambitious)
and they mostly seemed to fit my intuition that an unambitious person is quite passive, not really aiming to accomplish anything at all for any reason. So it seems to negate the whole idea of working hard with any goal, not only the goals suggested by "ambitious".
"Enterprising" is good (I think for everyone), and it's pretty close to "ambitious", which for me is somewhat bad. So it needs real research of the sort Irina Levontina did for the Russian usage. (Her article suggests to me that "aggressive" is also different in Russian and English, although I can think of some contexts where "aggressive" is positive in English too.)

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Irina Levontina's claim seems to be that агрессивный is nowadays used by some people as a positive characteristic; but this usage is new, so other people (and I belong to them) haven't yet adopted it and consider it strange and/or striking. For me, агрессивный макияж or агрессивная тактика (whatever it means) is not something I might find pleasant.

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