Woodland planting is gaining momentum as a potential method of natural flood management (NFM), due to its ability to break up soil and increase infiltration and water storage. In this study, a 2.2 km2 area in Warwickshire, England, planted with woodland every year from 2006 to 2012, was sampled using a Mini Disk infiltrometer (MDI). Infiltration measurements were taken from 10 and 200 cm away from the trees, from November 2019 to August 2021. Two individual hydrological models were built using the US Hydraulic Engineering Center Hydrological Modelling System (HEC-HMS), to model the effects of infiltration change on peak flows from the site throughout the summer and winter. The models were calibrated and validated using empirical data; the Nash and Sutcliffe Efficiency (NSE) was used as an indicator of accuracy. Results from this study show that woodland planting reduced peak flow intensity compared to impermeable land cover by an average of 6%, 2%, and 1% for 6-h, 24-h, and 96-h winter storms, respectively, and 48%, 18%, and 3% for 6-h, 24-h, and 96-h summer storms, respectively. However, grassland simulations show the greatest reduction in peak flows, being 32%, 21%, and 10%, lower than woodland for 6-, 24-, and 96-h winter storms, respectively, and 6%, 3%, and 0.5% lower than woodland for 6-, 24-, and 96-h summer storms, respectively.