Extreme heat can be harmful to human health and negatively affect athletic performance. The Tokyo Olympic and Paralympic Games are predicted to be the most oppressively hot Olympics on record. An interdisciplinary multi-scale perspective is provided concerning extreme heat in Tokyo—from planetary atmospheric dynamics, including El Niño Southern Oscillation (ENSO), to fine-scale urban temperatures—as relevant for heat preparedness efforts by sport, time of day, and venue. We utilize stochastic methods to link daytime average wet bulb globe temperature (WBGT) levels in Tokyo in August (from meteorological reanalysis data) with large-scale atmospheric dynamics and regional flows from 1981 to 2016. Further, we employ a mesonet of Tokyo weather stations (2009–2018) to interpolate the spatiotemporal variability in near-surface air temperatures at outdoor venues. Using principal component analysis, two planetary (ENSO) regions in the Pacific Ocean explain 70% of the variance in Tokyo’s August daytime WBGT across 35 years, varying by 3.95°C WGBT from the coolest to warmest quartile. The 10-year average daytime and maximum intra-urban air temperatures vary minimally across Tokyo (<1.2°C and 1.7°C, respectively), and less between venues (0.6–0.7°C), with numerous events planned for the hottest daytime period (1200–1500 hr). For instance, 45% and 38% of the Olympic and Paralympic road cycling events (long duration and intense) occur midday. Climatologically, Tokyo will present oppressive weather conditions, and March–May 2020 is the critical observation period to predict potential anomalous late-summer WBGT in Tokyo. Proactive climate assessment of expected conditions can be leveraged for heat preparedness across the Game’s period.