Conventional tool monitoring instruments are usually costly to acquire. The instruments are inadequate for real time wear measurement in the uncertain environmental conditions of developing countries. A modeling approach relating relevant parameters causing wear on cutting tools’ flank will be useful in predicting wear in machining operations. Mild steel turning experiment was carried out on the lathe using selected High Speed Steel (HSS) and High Carbon Steel (HCS) single point cutting tools. Speed, feed, and time of machining were varied accordingly, while running with, and without coolant. Hardness of the cutting tips of the tools was measured using Rockwell, R hardness tester. The corresponding speed, feed and time of machining were also noted. Turning operation was continued until the tool was totally blunt. At this stage recorded values of hardness, time of machining, feed and speed were modeled using multiple regression technique, with and without cutting fluid. The resulting models were strongly in agreement with the measured values. Therefore, the model is a good predictor of flank wear for the selected tools commonly used in developing countries. The findings showed that wear of the cutting tools can be predicted during machining at predetermined cutting conditions.