Convective heating is a key technology for in-situ pyrolysis of tar-rich coal. However, research on temperature and pressure characteristics, oil and gas generation mechanisms, and reaction zone characteristics under high-pressure, large-scale conditions remains limited. This study used a self-developed high-temperature, high-pressure in situ pyrolysis apparatus to conduct convective heating experiments on tar-rich coal from the eastern Ordos Basin. Temperature and pressure evolution was analyzed, while the oil and gas products and post-pyrolysis rock samples were characterized using GC/GC-MS, XRD, and CT analyses. The results were then compared with those obtained under conductive heating. The results indicate a significant enhancement in both pyrolysis efficiency and spatial sweep. The average heating rate reached 2.24 °C/h, which was 3.2 times that under conductive heating; meanwhile, the temperature-field homogenization rate was 5.15 times that under conductive heating, and the effective intense-pyrolysis volume fraction increased from 7.7% to 23.6%. Driven by strong dynamic carryover, oil and gas recovery was significantly improved. Oil production began 203 h earlier than under conductive heating. The cumulative oil and gas yields reached 24.48% and 92.42%, respectively, which were 12.42 times and 3.27 times the corresponding values under conductive heating. Reservoir flow conductivity was maintained, with an average permeability of 42.90 mD, 7.96 times the corresponding value under conductive heating. The local maximum porosity after pyrolysis reached 30.1%, and the area with porosity exceeding 14% accounted for 60%. The upward migration of low-density oil and gas products was more pronounced. Therefore, a horizontal well configuration with middle-lower injection and dual top-bottom production is recommended to maximize recovery efficiency. This study establishes a theoretical and experimental foundation for in-situ pyrolysis of tar-rich coal under convective heating.