Modeling approaches are presented for detecting an anomalous route to phase synchronization from time series of two interacting nonlinear oscillators. The anomalous transition is characterized by an enlargement of the mean frequency difference between the oscillators with an initial increase in the coupling strength. Although such a structure is common in a large class of coupled nonisochronous oscillators, prediction of the anomalous transition is nontrivial for experimental systems, whose dynamical properties are unknown. Two approaches are examined; one is a phase equational modeling of coupled limit cycle oscillators and the other is a nonlinear predictive modeling of coupled chaotic oscillators. Application to prototypical models such as two interacting predator-prey systems in both limit cycle and chaotic regimes demonstrates the capability of detecting the anomalous structure from only a few sets of time series. Experimental data from two coupled Chua circuits shows its applicability to real experimental system. (C) 2008 American Institute of Physics.