To understand and quantify casing wear during drilling operations, an experimental setup with real drill pipe joints (DPJ) and casings was designed and used to carry out wear tests, simulating various operating conditions and environments. P110 steel casing samples were tested under dry and wet conditions. Actual field oil- and water-based fluids were utilized to lubricate the contact area at two different side loads (1000 N and 1400 N) and DPJ speeds (115 and 207 rpm). The results show that for the same testing conditions, the casing wear volume and wear factor under water-based lubrication were more than twice those obtained under oil-based fluid testing. As expected, the wear volume and wear factor were highest under dry conditions. Moreover, it was noticed that, as the normal load was increased at a constant rotational speed (rpm), the wear factor increased. On the other hand, raising the rotational speed at the same applied load reduced the casing wear factor, due to the observed absence of adhesive wear and possible localized softening effects at higher speeds. SEM analyses of the worn areas showed that under dry conditions, the main wear mechanisms were abrasion and delamination. However, both adhesive wear and abrasive wear mechanisms were observed under oil-based lubrication. The energy dispersive spectroscopy (EDS) analysis of the worn surface revealed that at higher loads and speeds, a heavy transfer of particles from the oil-based lubricant took place. On the other hand, some contaminants of the water-based lubricant were observed on the worn surfaces.