Grease-lubricated rolling element bearings can suffer from wear due to lubricant starvation under certain oscillating operating conditions. Especially for large-scale slewing bearings, such as blade bearings in wind turbines, experimental investigations are complex compared to small-scale reference testing. For an easier manner of testing, it is desirable to know whether the results of small-scale testing are applicable to larger-sized bearings. In this work, three different bearing types were tested and compared to already published results from a small-scale ACBB with a pitch diameter of 60 mm. The newly tested bearing types comprise a downscaled blade bearing (4-point contact double row ball bearing) with a pitch diameter of 673 mm, a small-scale CRTB with a pitch diameter of 77.5 mm and another ACBB with a pitch diameter of 95 mm. Qualitatively, all tested bearings show similar wear behaviour in terms of friction energy when operation parameters are varied. With higher oscillation frequency, damage becomes more severe. The oscillation amplitude shows three distinctive regimes. Within the range of small amplitudes, an increase in amplitude leads to more pronounced damage. We observe a threshold amplitude where this is no longer the case; a further increase in amplitude counteracts wear initiation until a final threshold is reached, beyond which no more wear is observed. These findings are in accordance with the reference results of the small-scale ACBB. Direct comparison between point and line contact shows that the latter is more prone to wear initiation under grease-lubricated, oscillating operating conditions. Furthermore, a previously introduced empirical number shows good performance in assessing critical operating parameters of the different bearing types. Specifically, harmful operating conditions can be classified for all studied bearing types with an accuracy of 78%. This method can be useful to assess operating conditions of greased, oscillating, rolling element bearings, e.g., to assess different pitch controllers or designs of slewing bearings.