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A “classic generation” of seasonal learning research showed that many students lose academic skills over the summer months. Evaluations of summer interventions, largely aimed at-risk populations in American inner cities, generally show positive though mixed results. Summer interventions are becoming a standard educational practice across a range of regional and international settings, and as such require a new round of evaluations to reflect a greater range of program settings, structures and populations. This paper examines a summer numeracy intervention conducted in 2012 and 2013 for 589 attendees and 2,416 control students in grades 1-3 across multiple sites in Ontario, Canada. We employ a counterfactual framework to estimate a variety of propensity score matching models. We find that despite their pre-existing academic and social disadvantages, numeracy gains were greater among program attendees than among controls, with moderately strong effect sizes ranging from .12 to .18. We end by calling for more studies from other regional and international settings to add robustness to the body of empirical knowledge on summer learning interventions.