Urban overheating coincides with Heatwaves (HWs) and the thermal stress might get amplified in cities. To predict the interactions between urban overheating and HWs, the surface energy balance response to HWs is crucial. HW is a regional phenomenon and the climatic conditions may influence the local conditions to alter the energy budget contrast between a city and its adjacent peripheral areas. The interactions between the urban overheating and HWs are explored in a coastal city (Sydney Australia), also in the proximity of dry landmass, while considering the site characteristics, distance from the coast, and the population density. A positive response between urban overheating and HWs is reported. Advective heat flux in the form of a dualistic circulation system is found responsible for exacerbating the urban overheating magnitude (ΔT) during the HWs and altering the available energy balance. Land-coastal distance is also found as an important contributor in magnifying the urban-suburban temperature contrast. Considering the future urbanization in western Sydney, surfaces capable of retaining higher moisture content are prescribed to reduce the occurrence of extreme HW events. Activation of the ventilation corridor for the coastal wind penetration in western Sydney is another recommendation of this study. Unlabelled Image • Synergistic interactions between urban overheating and Heatwaves (HWs) are investigated. • Sensible, latent, and advective heat fluxes are examined. • Land-coast distance as an important contributor in exacerbating urban overheating. • Advective heat flux in the form of dualistic circulation as an important synergistic interaction. • Surfaces retaining higher moisture contents are prescribed in western Sydney. [ABSTRACT FROM AUTHOR]