Optimist International sponsors three scholarship contests for students to earn money to pursue opportunities in higher education: the Communication Contest for the Deaf and Hard of Hearing (CCDHH), the Essay Contest and the Oratorical Contest. The contests are conducted at the Club level, then Zone and Regional (if necessary) and at the District level. District-level scholarships are funded by the Optimist International Foundations and awarded by Optimist International.

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"iMagine" represents the organization's theme for 2019-2020 and it is written as shown for branding purposes. It does not replace the linguistic interpretation, intent, or spelling of the word "imagine or Imagine". As such, contestants are free to use the correct spelling for any contest or communications without penalty.