Usually means: Advantage aiding in achieving success.
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We found 15 dictionaries that define the word leg up:

General (9 matching dictionaries)
  1. leg up: Longman Dictionary of Contemporary English
  2. leg up: Merriam-Webster
  3. leg up: Oxford Learner's Dictionaries
  4. leg up: Collins English Dictionary
  5. leg-up: Wordnik
  6. leg up: Wiktionary
  7. leg up: Dictionary.com

Business (3 matching dictionaries)
  1. MoneyGlossary.com (No longer online)
  2. Leg up: Bloomberg Financial Glossary
  3. Leg up: Financial dictionary

Miscellaneous (1 matching dictionary)
  1. leg up: Idioms

Slang (1 matching dictionary)
  1. LEG-UP, leg up: Urban Dictionary

Sports (1 matching dictionary)
  1. Hickok Sports Glossaries (No longer online)

Definitions from Wiktionary (leg up)

noun:  The act of assisting another's progress over a wall or other obstacle by forming a step for one of their feet with one's hands.
noun:  (figuratively) A boost, a sudden improvement; an advantage, an edge.
noun:  (figuratively) Assistance, help given to get started or overcome a problem or obstacle.
verb:  (transitive, equestrianism) To walk a horse on a hard surface regularly.

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