Winter subsurface transport of the Pacific-origin warm water toward the Arctic Chukchi Borderland located west of the Canada Basin was investigated by mooring measurements and modeling analyses. In mid-winter or spring of 2011–2014, subsurface warming signals under sea ice were detected by the multi-year bottom-tethered mooring data in the Chukchi Abyssal Plain (CAP) of the western Chukchi Borderland. Lateral advection of shelf-origin ocean heat is a key process for the subsurface warming. To address the detailed pathways and processes of subsurface warm water transport, which have not been deeply explored, an interannual experiment for 2001–2014 was performed using a pan-Arctic sea ice-ocean model configured in a high-resolution framework. The horizontal grid size was set to approximately 5km so that narrow intense currents along complex sharp topography could be resolved. The model result captured the similar seasonality of subsurface temperature in the CAP region and produced interannual variability in the ocean heat content associated with the shelf-origin water distribution around the Chukchi Borderland. In addition to the Barrow Canyon throughflow, westward jets along the steep flank of the Chukchi shelf break constituted a primary pathway for the subsurface warm water transport toward the Chukchi Borderland in the model experiment. Since the simulated shelf break jet was much faster than main streams of the Beaufort Gyre, its role in ocean heat transport should be considered separately. Whereas ocean heat in the Chukchi shelf break region was partly lost via wind-driven turbulent mixing into upper halocline depths of approximately 20m, a substantial amount of the subsurface warm water remained even after mid-winter. The highly stratified condition due to anomalous sea ice meltwater assisted the winter heat transport.