Objectives The aim of our study was to identify, in mechanically ventilated neonates <30 weeks GA with clinical evidence of bronchopulmonary dysplasia (BPD), factors likely to be predictive of a first course of systemic dexamethasone leading to extubation within 14 days and remaining extubated for at least 7 days. Methods We studied a retrospective cohort of neonates (23+0-29+6 weeks GA), with evidence of BPD, prescribed their first course of systemic dexamethasone to aid in extubation from mechanical ventilation. The data collected only pertained to the first course of dexamethasone for any given neonate, with the primary outcome of interest of successful extubation within 14 days (i.e., extubated within 14 days of starting dexamethasone and remaining extubated for at least seven days). Binary logistic regression was employed. Results A total of 287 neonates were included. Each additional week of GA at birth led to a 1.53 increase in the odds of successful extubation (95% CI 1.122-2.096, p<0.01). Higher average fraction of inspired oxygen (FiO2) requirements in the preceding 24 hours resulted in a 0.94 decrease in the odds of successful extubation (p<0.05) and higher mean airway pressure (MAP) resulted in 0.76 decrease in odds of successful extubation (p<0.01). Conclusions Mechanically ventilated neonates born at <30 week GA, with evidence of BPD requiring dexamethasone to facilitate extubation, had a lower likelihood of successful extubation by day 14 if at the time of commencing steroids they were less mature at birth, had higher MAPs and higher oxygen requirements.