The emergence of high-rise buildings has necessitated frequent structural health monitoring and maintenance for safety reasons. Wind causes damage and structural changes on tall structures; thus, safe structures should be designed. The pressure developed on tall buildings has been utilized in previous research studies to assess the impacts of wind on structures. The wind tunnel test is a primary research method commonly used to quantify the aerodynamic characteristics of high-rise buildings. Wind pressure is measured by placing pressure sensor taps at different locations on tall buildings, and the collected data are used for analysis. However, sensors may malfunction and produce erroneous data; these data losses make it difficult to analyze aerodynamic properties. Therefore, it is essential to generate missing data relative to the original data obtained from neighboring pressure sensor taps at various intervals. This study proposes a deep learning-based, deep convolutional generative adversarial network (DCGAN) to restore missing data associated with faulty pressure sensors installed on high-rise buildings. The performance of the proposed DCGAN is validated by using a standard imputation model known as the generative adversarial imputation network (GAIN). The average mean-square error (AMSE) and average R-squared (ARSE) are used as performance metrics. The calculated ARSE values by DCGAN on the building model's front, backside, left, and right sides are 0.970, 0.972, 0.984 and 0.978, respectively. The AMSE produced by DCGAN on four sides of the building model is 0.008, 0.010, 0.015 and 0.014. The average standard deviation of the actual measures of the pressure sensors on four sides of the model were 0.1738, 0.1758, 0.2234 and 0.2278. The average standard deviation of the pressure values generated by the proposed DCGAN imputation model was closer to that of the measured actual with values of 0.1736,0.1746,0.2191, and 0.2239 on four sides, respectively. In comparison, the standard deviation of the values predicted by GAIN are 0.1726,0.1735,0.2161, and 0.2209, which is far from actual values. The results demonstrate that DCGAN model fits better for data imputation than the GAIN model with improved accuracy and fewer error rates. Additionally, the DCGAN is utilized to estimate the wind pressure in regions of buildings where no pressure sensor taps are available; the model yielded greater prediction accuracy than GAIN.