A promising approach for an effective shop scheduling that synergizes the benefits of the combinatorial optimization, supervised learning and discrete-event simulation is presented. Though dispatching rules are in widely used by shop scheduling practitioners, only ordinary performance rules are known; hence, dynamic generation of dispatching rules is desired to make them more effective in changing shop conditions. Meta-heuristics are able to perform quite well and carry more knowledge of the problem domain, however at the cost of prohibitive computational effort in real-time. The primary purpose of this research lies in an offline extraction of this domain knowledge using decision trees to generate simple if-then rules that subsequently act as dispatching rules for scheduling in an online manner. We used similarity index to identify parametric and structural similarity in problem instances in order to implicitly support the learning algorithm for effective rule generation and quality index for relative ranking of the dispatching decisions. Maximum lateness is used as the scheduling objective in a job shop scheduling environment.