Subcooled liquid vapor pressures (P(L)) are of great importance for assessing the persistent behavior of organic pollutants. As P(L) cannot be determined by direct experiments, it is of interest to develop and evaluate various predictive methods. In the current study, gas chromatography retention index (GC-RI) and quantitative structure-property relationship (QSPR) methods were used to develop predictive models for P(L) of polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs). The model development was based on P(L) values converted from consistent experimental solid vapor pressures (P(S)). The P(L) values predicted by the two methods are highly consistent with each other, and in-between sets of values predicted by others. Since the QSPR method can be regarded as independent of experiments, and can be used to interpret intermolecular interactions that govern the magnitude of P(L), it may be superior to the GC-RI method.