Wintertime sea surface temperature (SST) cooling south of the Indian tip (hereafter tip) is investigated during a 14 day gap wind event (21 January to 3 February 1997) using satellite data and the three-dimensional, primitive equation, sigma coordinate Princeton Ocean Model (POM). The advanced very high resolution radiometer SST reveals surface cooling of 1.5¿C over the 14 day period near west of Sri Lanka. A spatial-mean time series of surface forcing west of Sri Lanka indicate a bell-shaped pattern, which is characterized by maximum wind stress and outgoing heat flux (sum of turbulent heat flux and net surface long-wave radiation) of 0.12 N/m2 and 450 W/m2, respectively, on 27 January. POM simulation is performed with realistic bottom topography, with seasonal stratification, and with daily mean surface forcing derived from NASA scatterometer (NSCAT) winds and National Centers for Environmental Prediction (NCEP)/National Center for Atmospheric Research (NCAR) meteorological variables. During 21--28 January, Ekman dynamics together with positive wind stress curl promote SST cooling along the west coast of Sri Lanka. Thereafter irregular and shallow topography near the tip promotes diapycnal mixing, and the characteristic surface circulation significantly influences the evolution of the SST pattern along the periphery of the tip. An anticyclonic circulation evolves in the Gulf of Mannar under the influence of local negative wind stress curl after 27 January. Examination of a zonal section of density and vertical heat diffusion reveals that the initial stratification in the vicinity of the tip weakens because of diapycnal mixing and vertical diffusion of the surface heat. The mixed layer heat budget near the west of Sri Lanka and south of the tip reveals that the surface heat depletion dictates SST changes throughout the event. From our earlier works <Luis and Kawamura, 2000, 2001> and from the results of the present investigation it is inferred that the wintertime SST cooling in the vicinity of the tip is a case of topography-monsoon-ocean interaction.