Usually means: Calm, composed under stress, pressure.
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We found 5 dictionaries that define the word cool head:

General (4 matching dictionaries)
  1. cool head: Merriam-Webster
  2. cool head: Wiktionary

Slang (1 matching dictionary)
  1. Cool Head: 1960's Slang

Definitions from Wiktionary (cool head)

noun:  (idiomatic) A calm, focused demeanor and mindset; a person having such characteristics.

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