| Competition: | Cayman Islands Premier League |
| Season: | 2019–20 |
| Winners: | Bodden Town FC |
| Relegated: | Alliance FC North Side SC |
| Continentalcup1: | Caribbean Club Shield |
| Continentalcup1 Qualifiers: | Bodden Town FC |
| League Topscorer: | Kimani Finn (Scholars International) Chris Reeves (Elite) |
| Biggest Home Win: | (9 February 2020) |
| Biggest Away Win: | (7 December 2019) |
| Highest Scoring: | (2 November 2019) (9 February 2020) |
| Matches: | 66 |
| Total Goals: | 230 |
| Longest Wins: | 8 matches (Bodden Town) |
| Longest Unbeaten: | 8 matches (Bodden Town) |
| Longest Losses: | 11 matches (North Side) |
| Longest Winless: | 11 matches (North Side) |
| Prevseason: | 2018–19 |
| Nextseason: | 2020–21 |
The 2019–20 Cayman Islands Premier League was the 41st edition of top tier Cayman Islands Premier League football competition in the Cayman Islands. The season began on 19 October 2019.[1] The season was indefinitely postponed on 12 March 2020, due to the COVID-19 pandemic.[2] The season was resumed on 15 August.[3]
Scholars International unsuccessfully defended its 2018 title. Bodden Town successfully pursued its 4th title in the 2020 final.