Modern studies suggest that the upper ocean heat content (OHC) in the tropical Indian Ocean (TIO) is a better qualitative predictor of the Indian summer monsoon rainfall (ISMR). But it is still unknown how the OHC is mechanically linked to ISMR and whether it can be applied to long-term climate changes. By analyzing reanalysis datasets across the 20th century, we illustrate that in contrast to those anomalies associated with stronger ISM westerlies, higher ISMR is accompanied with summer surface high pressure and east wind anomalies from the South China Sea to the Bay of Bengal (BOB), and is loosely related to increased western TIO OHC during decayed phases of positive Indian Ocean dipole (IOD) and of El Niño. Except for 1944–1968 AD, this interannually lagged ISMR response to winter OHC is insignificant, probably suppressed by those simultaneous effects of positive IOD and El Niño on ISMR. In our paleoclimatic simulations, this modern observed lagged response is interrupted by seasonally reversed insolation anomalies at the 23,000-year precessional band. Our sensitivity experiments further prove that, the ISMR can be simultaneously reduced by positive IOD-like summer OHC anomalies both for modern and precessional situations. This damping effect is mainly contributed by the warmer western TIO that triggers anomalous surface high pressure, easterly winds, and drastically reduced rainfall from BOB to Arabian Peninsula, but with slightly increased rainfall in the northern ISM region. And the cooler southeastern TIO will only moderately increase rainfall in the southern ISM region.