Abstract Boreal summer intraseasonal oscillation (BSISO) is a primary source of predictability for summertime weather and climate on the subseasonal-to-seasonal (S2S) time scale. Using the GFDL SPEAR S2S prediction system, we evaluate the BSISO prediction skills based on 20-yr (2000–19) hindcast experiments with initializations from May to October. It is revealed that the overall BSISO prediction skill using all hindcasts reaches out to 22 days as measured by BSISO indices before the bivariate anomalous correlation coefficient (ACC) drops below 0.5. Results also show that the northeastward-propagating canonical BSISO (CB) event has a higher prediction skill than the northward dipole BSISO (DB) event (28 vs 23 days). This is attributed to CB’s more periodic nature, resulting in its longer persistence, while DB events are more episodic accompanied by a rapid demise after reaching maximum enhanced convection over the equatorial Indian Ocean. From a forecaster’s perspective, a precursory strong Kelvin wave component in the equatorial western Pacific signifies the subsequent development of a CB event, which is likely more predictable. Investigation of individual CB events shows a large interevent spread in terms of their prediction skills. For CB, the events with weaker and fluctuating amplitude during their lifetime have relatively lower prediction skills likely linked to their weaker convection–circulation coupling. Interestingly, the prediction skills of individual CB events tend to be relatively higher and less scattered during late summer (August–October) than those in early summer (May–July), suggestive of the seasonal modulation on the evolution and predictability of BSISO. Significance Statement The advance of subseasonal-to-seasonal (S2S) prediction largely depends on dynamical models’ ability to predict some major intrinsic modes in the climate system, including the boreal summer intraseasonal oscillation (BSISO). Using a newly developed S2S prediction system, we thoroughly evaluated its performance in predicting BSISO, and revealed the skill dependence on the BSISO propagation diversity. Here we provide physical explanations of what influences the BSISO predictions and identify different precursory signals for two types of BSISO, which have important implications for operational forecasts.