Usually means: First-year cadet at military academy.
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We found 10 dictionaries that define the word doolie:

General (9 matching dictionaries)
  1. doolie: Merriam-Webster
  2. doolie: Oxford Learner's Dictionaries
  3. doolie: Collins English Dictionary
  4. doolie: Wordnik
  5. doolie: Wiktionary
  6. doolie: Webster's New World College Dictionary, 4th Ed.
  7. doolie: Infoplease Dictionary
  8. doolie: Dictionary.com
  9. doolie: FreeDictionary.org

Slang (1 matching dictionary)
  1. doolie: Urban Dictionary

Definitions from Wiktionary (doolie)

noun:  (US) A first-year student at the United States Air Force Academy; a cadet freshman.
noun:  (India, chiefly historical) Alternative form of dooly (“basic Indian litter; stretcher; litter”) [(India, now chiefly historical) A basic Indian litter or sedan chair made of poles, ropes, and a seat or cloth.]

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