A method and a system for conducting a static timing analysis on a circuit having a plurality of point-to-point delay constraints between two points of the circuit, in which two conservative and two optimistic user defined tests are derived for all types of the point-to-point delay constraints. The method shows that when a conservative test is performed without introducing any special tags, then it is found that the point-to-point constraint is satisfied. On the other hand, when the optimistic test fails without any special tags, it is determined that the point-to-point constraint is bound to fail if special tags are introduced, in which case, they are to be introduced only when an exact slack is desired. Finally, for anything in between, a real analysis with special tags or path tracing is required. Based on the topology of the graph, arrival time based tests may be tighter in some situations, while the required arrival time based tests, may be tighter in others.