Farmers are looking for appropriate tools for assessing and interpreting the health status of their soils; however, there is no standardized and prairie-based soil health scoring framework. Accordingly, we focused on developing one for arable cropping systems in Saskatchewan. In 2018, soil samples (0–15, 15–30, and 30–60 cm depths) were collected from 55 arable fields across Saskatchewan, along with native prairie samples. Various soil chemical, physical, and biological attributes were measured (23 attributes in total). Based on the data distribution for each attribute, we developed scoring functions. The results from multivariate analyses were used to determine the weighting factors needed to integrate the individual scores from each soil attribute into a single Saskatchewan Assessment of Soil Health score. Soil carbon (C) and nitrogen (N) indices (soil organic C, active C, total N, and soil protein) and total phosphorus produced the highest weighting factors. We also tested if there were linkages between the soil health and crop productivity by assessing the cereal yields for the past 10 years as reported from the same rural municipalities where the soil samples were collected. A positive relationship between soil health and yields was most apparent during dry years; thus, we recommend further research to explore this linkage at a finer scale. Overall, this research forms the foundation of a promising framework that can be built upon, and in due course, lead to the development of a tool for producers who are interested in tracking soil health and using the results to inform management.