Gray Cast Iron Casting (GCIC) materials are widely used particularly in automotive industries. However, the high cost of processing these materials limits the use of their improved mechanical properties. Tool life is one of the most important factors in machining operations of such materials and it is mainly affected by cutting conditions including the cutting speed, depth of cut, insert material and cooling environment along with length and diameter of the tool body. In addition, the modern industry is moving towards automating the manufacturing processes. Therefore, tool life monitoring is important to achieve an efficient manufacturing process. In this study, a tool wear prediction model during the boring machining operation of gray cast iron is studied. It is based on the monitoring of tool performance in controlled machining tests with measurements of tool life, surface finish, bore size variation, cutting time and load on spindle in terms of % current under different combinations of cutting parameters (cutting speed, depth of cut, tool nose radius, length & diameter of tool, tool material and coolant pressure & concentration). The influence of cutting parameters on the tool life was studied experimentally by performing more than 120 cutting tests. A prediction model was then developed to predict tool wear. The basic steps used in generating the model adopted in the development of the prediction model are: collection of data; analysis, pre-processing and feature extraction of the data, design of the prediction model, training of the model and finally testing the model to validate the results and its ability to predict tool wear. The evolution of boring machining operation properties using different parameters is a complex phenomenon. There are many factors (like cutting speed, depth of cut, insert material and cooling environment along with length and diameter of the tool bodyaffecting the performance of cast iron boring machining operation resulting to poor tool life. This paper presents an experimental investigations and Sequential classical experimentation technique has been used to perform experiments for various independent parameters. An attempt of mini-max principle has been made to optimize the range bound process parameters for minimizing cutting time and surface finish during cast iron boring machining operation. The test results proved that cutting time and surface finish were significantly influenced by changing important four dimensionless π terms. The process parameters grouped in π terms were suggested the effective guidelines to the manufacturer for improving tool life by changing any one or all from theavailable process parameters.