Introduction: Apgar scoring in modern practice has extended beyond the original described remit by Virginia Apgar, including prognostication. Prognostic value of Apgar scoring in preterm populations is unsupported by robust evidence. Objectives: We aimed to identify the association between mortality or a composite mortality/major morbidity outcome in preterm infants with 1-min, 5-min, and sum 1 + 5-min Apgar scores. Methods: Seven-year retrospective data was analysed on neonates born <32 weeks gestation in a regional neonatal centre. Co-primary outcomes were mortality and composite mortality/major morbidity. Adjusted odds ratios (aOR) were estimated using multivariable logistic regression analysis. Results: 394 infants were included in the analysis. In neonates born <28 weeks gestation, no significant association was found between Apgar scores and the co-primary outcomes. In neonates born ≥28 weeks, low 1-min (aOR 10.452 [1.273, 85.835] for scores 4–6, 22.173 [2.666, 184.438] for scores 0–3), 5-min (4.724 [1.616, 13.806] for scores 4–6, 11.178 [1.803, 69.299] for scores 0–3), and sum 1 + 5-min Apgar scores (12.447 [2.674, 57.941] for scores 4–6, 55.960 [8.333, 375.804] for scores 0–3) were associated with significantly increased aOR of mortality. Increased aOR of composite mortality/major morbidity were also seen in neonates with moderately low (4–6) Apgar scores (aOR 3.104 [1.522, 6.328] for 1 min, 2.804 [1.406, 5.594] for 5 min, and 3.232 [1.769, 5.905] for 1 + 5 min). Conclusions: Apgar scoring at 1 and 5 min has limited prognostic accuracy for extremely preterm infants but is prognostic in older infants. Sum Apgar scores, a measure of initial condition and response to resuscitation, may be a better predictor of mortality than individual scores.