When railway vehicles run on sharp curves, the coefficient of friction (COF) between the outer rail and the leading-outside wheel flange of a bogie is an important value related to problems such as wheel/rail severe wear, squeak noise arising from wheel/rail contact, and running safety against flange-climb derailment. In general, it is difficult to grasp the actual state of COF, which changes from moment to moment during commercial operations. From the viewpoint of running safety and maintenance, it is desirable to detect curved tracks with relatively high COF from the entire service line. The monitoring bogie, which can measure wheel/rail contact forces during commercial operations, has realized a long-term observation of wheel/rail contact forces. For further applications of the monitoring bogie, the simulation-based estimation method of COF at the wheel flange have been proposed in the author’s previous paper. Furthermore, an investigation based on roller-rig tests have been conducted. However, the probability of the flange wear progress cannot be determined only by COF at the wheel flange, and other factors should be involved. The wear number is used to assess rolling contact fatigue and wheel/rail wear progress. In the present paper, on the basis of a multi-body dynamics simulation model of the roller-rig equipment, the difference of the wear number among four lubrication conditions on the bogie is clarified. The estimation method of COF is extended to estimate the wear number simultaneously. The extended method is applied to the roller-rig test and the wear number is estimated. The estimated wear number shows qualitative agreement with the amount of wear debris, which is observed in the roller-rig test conducted in previous research.