| Competition: | Cayman Islands Premier League |
| Season: | 2018–19 |
| Winners: | Scholars International |
| Continentalcup1: | Caribbean Club Shield |
| Continentalcup1 Qualifiers: | Scholars International |
| Prevseason: | 2017–18 |
| Nextseason: | 2019–20 |
The 2018–19 Cayman Islands Premier League season was the 40th edition of top tier Cayman Islands Premier League [Association football|football]] competition in the Cayman Islands. The season began on 3 November 2018.[1] The season ended on 17 March 2019.
Scholars International successfully defended its 2018 title in the 2019 final for its 12th successive title.
The 4 November match between North Side and Tigers was abandoned following a fight between the two clubs, causing both clubs to be awarded a 0–3 loss.