South Africa participated in TIMSS from 1995 to 2015. Over these two decades, some positive changes have been reported on the aggregated mathematics performance patterns of South African learners. This paper focuses on the achievement patterns of South Africa's high-performing Grade 9 learners (n = 3378) in comparison with similar subsamples of learners from Australia (n = 6581) and England (n = 3439) whose education systems are regarded as comparable. The aim of this study is to describe the relative strengths and weaknesses of these learners with reference to a selected subset of the TIMSS-2011 items comprising multiplicative concepts. The focus is on a specific though important content subdomain, the multiplicative conceptual field, which is considered a crucial learning area at this phase of schooling. The percentage correct scores were compared. In addition a Rasch analysis was applied to render both item difficulty and person proficiency on a single scale. In particular, the research outcome shows that this subset of South African Grade 9 students is able to solve routine problems, but lacks proficiency when it comes to application-type or reasoning-type problems. The Australian and English subsets show comparable strengths across all three problem types. We conclude that the factors determining performance include mathematical difficulty. However, where radically different outcomes across the three countries emerge, such differences may be explained by country-specific curricula implementation.