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The observation-reanalysis difference method (OMR) and wind profile fitting method were used to analyze the influence urbanization has on the near-surface wind speed in Shanghai during tropical cyclone events. The data used include daily wind speed data from the Shanghai Meteorological Observatory Station collected from 1991 to 2020, hourly wind speed data from 100 meter high wind towers from 2017 to 2019, and reanalysis data that covered the same period. The results indicated that during tropical cyclone occurrence, the wind speed of the OMR in the central urban region was significantly lower than that in the suburban area, and the OMR declined more obviously over the year, down to -8 m/s in 2020. Urbanization leads to the increase of average wind weakening rate to be higher than the maximum wind weakening rate, causing the maximum weakening rate of the central urban region to the average wind over 80%, while maximum wind speed was less than 80%. The weakening rate of both the average and maximum wind speeds during tropical cyclone impacts is greater than the rate that the annual average wind speed was reduced. A logarithmic variation was visible in the wind profile of the island station during tropical cyclone occurrence, with an average friction velocity U* of 0.9389 m/s and an average rough length Z0of 0.4915 m. The wind speed during tropical cyclone events was higher than the three-year average wind speed within each layer. The suburban stations show a linear variation, and every hundred meters of height results in an increase of 5–6 m/s in the wind speed change rate. At 100 meters of altitude, the wind speed in the suburban region is reduced by approximately 40%.