Crop yield is influenced over time and space, namely, by a wide range of variables linked with crop genetics, agronomic management practices and the environment under which the crop dynamically responds to maximize growth potential and survival. Such variability can pose substantial uncertainty and risks in the use of agricultural sustainability decision-making frameworks that include crop yield as a leading metric. Here, decision analytics can play a vital role by guiding the use of statistical-based analytics to build in a higher degree of intelligence to enable better predictive (i.e., crop yield forecasting both over the growing season and inter-annually) and prescriptive (optimization across crop areas and subdivisions) approaches. While inter-annual variability in yield can be modelled based on a deterministic trend with stochastic variation, quantifying the variability of yield and how it changes across different spatial resolutions remains a major knowledge gap. To better understand how yield scales spatially, we integrate in this study, for the first time, multi-scale crop yield of spring wheat and its variance (i.e., field to district to region) obtained within the major wheat growing region of the Canadian Prairies (Western Canada). We found large differences between the mean and variance from field to district to regional scales, from which we determined spatially-dependent (i.e., site specific) scaling factors for the mean and variance of crop yield. From our analysis, we provide several key recommendations for building capacity in assessing agricultural sustainability using spatial-based metrics. In the future, the use of such metrics may broaden the adoption and consistent implementation of new sustainable management protocols and practices under a precautionary, adaptive management approach.