Might mean (unverified): Rooting for the less favored side.
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We found one dictionary that defines the word underdoggish:

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  1. underdoggish: Wiktionary

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Definitions from Wiktionary (underdoggish)

▸ adjective:  Characteristic of an underdog.

Similar:
hangdog, hangdoggy, doggy, hoodlumish, dogwater, ne'er-do-well, doggrel, maverickish, draggle-tail, bulldykish, more...

Opposite:
dominant, favored, superior, top dog

▸ Words similar to underdoggish

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Similar:
hangdog, hangdoggy, doggy, hoodlumish, dogwater, ne'er-do-well, doggrel, maverickish, draggle-tail, bulldykish, more...

Opposite:
dominant, favored, superior, top dog



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