Usually means: Unexpected event influencing November elections.
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We found 6 dictionaries that define the word October surprise:

General (5 matching dictionaries)
  1. October surprise: Merriam-Webster
  2. October surprise: Oxford Learner's Dictionaries
  3. October surprise: Collins English Dictionary
  4. October surprise: Wiktionary
  5. October Surprise, October surprise: Wikipedia, the Free Encyclopedia

Miscellaneous (1 matching dictionary)
  1. October surprise: Wordcraft Dictionary

Definitions from Wiktionary (October surprise)

noun:  (US politics) An occurrence that unexpectedly comes to public attention just prior to a November election, especially a presidential election, and that is likely to affect the outcome.

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