Today's compilers offer a huge number of transformation options to choose among and this choice can significantly impact on the performance of the code being optimized. Not only the selection of compiler options represents a hard problem to be solved, but also the ordering of the phases is adding further complexity, making it a long standing problem in compilation research. This paper presents an innovative approach for tackling the compiler phase-ordering problem by using predictive modeling. The proposed methodology enables i) to efficiently explore compiler exploration space including optimization permutations and repetitions and ii) to extract the application dynamic features to predict the next-best optimization to be applied to maximi...