Usually means: Inexperienced recruits struggling with training.
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We found 9 dictionaries that define the word awkward squad:

General (9 matching dictionaries)
  1. awkward squad: Merriam-Webster
  2. awkward squad: Wordnik
  3. awkward squad: Wiktionary
  4. Awkward squad: Dictionary.com
  5. Awkward squad (trade unionists), Awkward squad: Wikipedia, the Free Encyclopedia
  6. Awkward Squad: Dictionary of Phrase and Fable (1898)
  7. awkward squad: FreeDictionary.org
  8. Awkward squad: TheFreeDictionary.com
  9. awkward squad: Merriam-Webster

Definitions from Wiktionary (awkward squad)

noun:  (military) A squad of inept recruits assembled for special drill.
noun:  A group of inept or incompetent individuals in an organization.

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