Data on the burden of extended-spectrum β-lactamase producing Enterobacterales are limited in Jamaica. This study aims to identify factors associated with the isolation of ceftriaxone-resistant Enterobacterales in patients at a private hospital in Jamaica through a retrospective case-control study comparing patients with and without ceftriaxone-resistant Enterobacterales in 2021. The case subjects had at least one Enterobacterales isolate resistant to ceftriaxone, and the controls had at least one culture, all without cephalosporin resistance, including those without growth. The data extracted included antibiotics received, organism, sex, and age. Older age, male sex, and the isolation of Enterobacter species were independently associated with increased odds of ceftriaxone-resistant Enterobacterales on logistic regression. Age and male sex may be markers for past exposure to β-lactam antibiotics or nosocomial infection with ceftriaxone-resistant Enterobacterales and may have a greater influence on isolation of ceftriaxone-resistant Enterobacterales compared with the receipt of antibiotics in the past six months, with which no association was observed on final analysis.