Urban overheating (UO) may interact with synoptic-scale weather conditions. The association between meteorological parameters and UO has already been a subject of considerable research, however, the impact of synoptic-scale weather conditions on UO magnitude, particularly in a coastal city that is also near the desert landmass (Sydney) has never been investigated before. The present research examines the influence of synoptic-scale weather conditions on UO magnitude in Sydney by utilizing the newly developed gridded weather typing classification (GWTC). The diurnal, and seasonal variations in suburban-urban temperature contrast (ΔT) in association with synoptic-scale weather conditions, and ΔT response to synoptic air-masses during extreme heat events are investigated in three zones of Sydney. Generally, an exacerbation in UO magnitude was reported at daytime over the years, whereas the nocturnal UO magnitude was alleviated over time. The humid warm (HW), and warm (W) air-masses were found primarily responsible for exacerbated daytime UO during extreme heat events and in all other seasons, raising the mean daily maximum ΔT to 8-10.5 °C in Western Sydney, and 5-6.5 °C in inner Sydney. The dry warm (DW), and W conditions were mainly responsible for urban cooling (UC) at nighttime, bringing down the mean daily minimum ΔT to - 7.5 to - 10 °C in Western Sydney, and - 6 to - 7.5 °C in inner Sydney. The appropriate mitigation technologies can be planned based on this study to alleviate the higher daytime temperatures in the Sydney suburbs.