Both the American Society of Anesthesiologists and the UK NAP4 project recommend that an unspecified pre-operative airway assessment be made. However, the choice of assessment is ultimately at the discretion of the individual anaesthesiologist. We retrieved a cohort of 188 064 cases from the Danish Anaesthesia Database, and investigated the diagnostic accuracy of the anaesthesiologists' predictions of difficult tracheal intubation and difficult mask ventilation. Of 3391 difficult intubations, 3154 (93%) were unanticipated. When difficult intubation was anticipated, 229 of 929 (25%) had an actual difficult intubation. Likewise, difficult mask ventilation was unanticipated in 808 of 857 (94%) cases, and when anticipated (218 cases), difficult mask ventilation actually occurred in 49 (22%) cases. We present a previously unpublished estimate of the accuracy of anaesthesiologists' prediction of airway management difficulties in daily routine practice. Prediction of airway difficulties remains a challenging task, and our results underline the importance of being constantly prepared for unexpected difficulties.