This paper investigates the application of heterodyned Acoustic Emission (AE) compared to more conventional vibration measurements for Condition Monitoring (CM) of an offshore drilling machine, with a particular focus on the large, axial tapered roller bearing supporting the drill string weight in a top drive. The focus on cost reduction and operational uptime in the oil and gas industry motivates research on improved CM methods for fault detection, identification and ultimately prediction. However, bearing failure on this type of machines are currently responsible for a significant share of operational downtime on drilling rigs. In the experiment, a previously used and replaced bearing is compared to a new, healthy bearing with the purpose of identifying possible condition indicators (CI) from the vibration and AE measurements. AE root-mean-square values (RMS) was identified as a CI, being more consistent with the expected bearing health than vibration measurements and also less affected by operating speed. The AE measurements also show complementary forced frequency identification capabilities compared to the vibration measurements. The particular failure mode with bearing roller end damage is described and seen in conjunction with the results.