The Coupled Ocean-Atmosphere-Wave-Sediment Transport (COAWST) model has been employed to simulate the anomalous post-monsoon tropical cyclone (TC) Jawad that originated over the Bay of Bengal (BoB) in December 2021. The atmospheric initial and boundary conditions (IC and BC) have been obtained from the Global Forecasting System (GFS) Analyses and Forecasts and two contrasting ocean IC and BCs, viz., HYCOM (experiment name GFS-HYCOM) and INCOIS (experiment name GFS-INCOIS), are implemented in two separate coupled experiments to evaluate the influence of TC Jawad on the surface and sub-surface characteristics of BoB. The track of the TC, including its recurvature, was well captured by both experiments with significant accuracy. A proper contrast in temperature between the two sides of the TC track was noted in the surface and sub-surface temperatures observed by two buoys, i.e., (1) BD11 (west of the TC track) and (2) BD13 (east of the TC track), and the simulated temperatures were validated with these observations. Contrary to the usual scenario, the higher sub-surface warming on the eastern side of the TC track was captured by GFS-HYCOM, but with a significant overestimation. The lower temperature on the western side of the TC track can be attributed to the weak upwelling associated with the cyclonic circulation caused by the interaction of the TC with the southward coastal currents. An unusually higher downwelling on the eastern side of the TC track was observed in the vertical distribution of the temperature across the longitudes, which suggested the existence of a strong clockwise circulation near the location of BD13. GFS-HYCOM, which simulated a higher current magnitude in the sub-surface than GFS-INCOIS on the eastern side of the TC track, captured the circulation near BD13 more rigorously. From further analysis, it was inferred that the interaction of the cyclonic wind flow of TC Jawad (westerly) near the surface with the easterly flow caused the generation of the clockwise circulation over the ocean surface on the eastern side of the TC track, leading to intense downwelling and warming of the sub-surface temperature. This scenario was further corroborated by the simulated Ekman transport and higher convective activity in the eastern quadrants of the TC. The present study not only emphasizes the capability of the coupled ocean-atmosphere models to simulate TCs but also highlights the necessity of investigating the air-sea interaction processes and their responses to the passage of an anomalous TC like Jawad.