The drilling process is highly non-linear. Coupled with a thermo-mechanical machining, localized heating and temperature increases in the workpiece are caused by the rapid plastic deformation of the workpiece and by the friction along the drill-chip interface. The cutting temperature at the tool-chip interface is an important factor which directly affects workpiece surface integrity, tool wear, and hole diameter and cylindricity in the drilling process. In this study, the effects of sequential dry drilling operations on the drill bit temperature were investigated both experimentally and numerically. Drill temperatures were measured by inserting standard thermocouples into the coolant (oil) hole of TiN/TiAlN-coated carbide drills. Experimental studies were conducted using two different workpiece materials, AISI 1040 steel and Al 7075-T651. The drill bit temperature was predicted using a numerical computation with Third Wave AdvantEdge finite element method (FEM) software, which is based on Lagrangian explicit. The results obtained from the experimental study and finite element analyses (FEA) were compared. Reasonable agreement between the measured and calculated drill bit temperature results were found for sequential dry drilling.