This study was carried out to investigate the impact the quality of the drill bits has on the machining behavior of additive manufacturing (AM) and powder metallurgy (PM) titanium alloys. Therefore, commercially available drill bits which typically reflect two extremes of drill bit quality were selected. The performance of coated carbide twist drills, typically recommended for the drilling of wrought titanium alloys was compared with that of high-speed steel (HSS) drills. The average torque value, specific cutting energy (SCE), and tool wear were used to evaluate the drilling performance of AM and PM titanium alloys. The results of drilling tests revealed the application of the coated carbide drill resulted in lower torque and SCE values, less flank wear, and lower build-up-edge (BUE) compared with the uncoated HSS drill bits for AM fabricated titanium alloys. However, the carbide drill appeared to offer negligible improvement over the uncoated HSS drill when employed with the PM fabricated titanium alloy. In spite of the improvement in the drilling performance offered by the carbide drills for the AM titanium alloy, TiB intermetallic particles (part of the AM titanium microstructure) contributed to the damage of the coated carbide drill which would limit the drill lifetime.