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In addition to the Taiwan Strait, the geographical channel effect (GCE) has been observed in the Taipei Basin during winters. This study explored the potential links amongst GCE phenomena in the basin, fine particulate matter (PM2.5) events, and position of the continental high-pressure system (CHPS). Principal component analysis was applied to classify the CHPS distribution patterns influencing PM2.5 concentrations and meteorological parameters in the Taipei metropolis. In addition, non-parametric Kruskal–Wallis and Dwass–Steel–Critchlow–Fligner tests were applied to compare the parameters amongst distinct groups. Moreover, track analysis was utilised to trace the trajectories of air masses. The merged Dark Target Aerosol Angstrom Exponent (Ocean), Deep Blue Aerosol Angstrom Exponent (Land), and Aerosol Optical Depth (AOD) 3 km (Land and Ocean) of Terra/MODIS and Aqua/MODIS were used to confirm the connection of long-range PM2.5 transport. Two features in the atmospheric environment induce double GCEs: (1) wind direction below 90° in most of the upwind area of the Taisumi and Xindian River Basins; (2) CHPS centres moved across 110° E. Double GCEs can reduce the magnitude of PM2.5 air pollution and shape the distribution of PM2.5; however, they cannot prevent PM2.5 events. [ABSTRACT FROM AUTHOR]