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The characteristics of 21 tropical cyclones (TCs) and associated high winds in Shanghai from 2005 to 2020 are analyzed based on the TC best track data, surface observations, and ERA5 reanalysis dataset. Results indicate that 95% of the TCs causing high winds in Shanghai were generated during July to September, and located to the south of Shanghai for ~80% of the impact time. Divided into four categories according to tracks, the TCs show significant discrepancies in genesis month and location, intensity, size, and duration. The findings of high winds in Shanghai highlight the combination effect of TC intensity, track, and the distance between TCs and Shanghai normalized by TC size (NDSH-TC). The maximum 10‐min sustained (Vmax) and extreme 3‐s wind speeds (Vex) in Shanghai only increase slightly with TC intensity, due to the fact that the stronger TCs are usually farther away from Shanghai. The Vmax and Vex differ in response to different TC tracks and reach the maximum value under TCs moving northward across the land west of Shanghai and the sea east of Shanghai, respectively. The urban and coastal wind speeds are the smallest and the largest respectively, indicating that the largest underlying surface roughness is associated with the most rapid urban construction. The wind speeds under the influence of TCs in four quadrants of Shanghai also present different variations with the NDSH-TC. Additionally, the wind direction in Shanghai is regularly related to the relative position between the TC center and Shanghai. A case study combined with TC In‐Fa (2106) verified the validity of the conclusions, which can provide a reference for TC forecasters to make more accurate wind field predictions. [ABSTRACT FROM AUTHOR]