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Answer for the clue "Occupying the cellar ", 9 letters:
losingest

Word definitions for losingest in dictionaries

Wiktionary Word definitions in Wiktionary
a. The most losing; who has lose most games, votes, etc.

Usage examples of losingest.

It was a fishbone of resentment lodged deep in his throat, proof against all psychological Heimlich maneuvers, that the Bobcats were the losingest team in the history of Little League, baseball, and American sport.