Usually means: Having the most losses recorded.
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We found 6 dictionaries that define the word losingest:

General (6 matching dictionaries)
  1. losingest: Oxford Learner's Dictionaries
  2. losingest: American Heritage Dictionary of the English Language
  3. losingest: Wordnik
  4. losingest: Wiktionary
  5. losingest: Dictionary.com
  6. losingest: Dictionary/thesaurus

Definitions from Wiktionary (losingest)

adjective:  (US, sports) The most losing; who has lost most games, votes, etc.

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