Usually means: Stay calm under pressure always.
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We found 3 dictionaries that define the word keep a cool head:

General (3 matching dictionaries)
  1. keep a cool head: Merriam-Webster
  2. keep a cool head, keep a cool head: Cambridge Advanced Learner's Dictionary
  3. keep a cool head: Wiktionary

Definitions from Wiktionary (keep a cool head)

verb:  (idiomatic) To keep one's cool; to stay calm.

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