This study conducted an analysis of selected items from the Caribbean Secondary Education Certificate (CSEC) mathematics multiple-choice test to detect misunderstandings or misconceptions among Jamaican test-takers. The sample of the data included 7,000 CSEC test-takers’ test scores for the examination period 2010–2016. The study applied the Classical Test Theory (CTT) and the Item Response Theory (IRT) in the data analysis process. Results from the study showed that the CSEC mathematics multiple-choice test recorded a relatively high distractor efficiency (DE) for each exam year over the period 2010–2016; and the items were less prone to guessing, based on Jamaican test-takers’ responses. The CTT item difficulty analysis showed that Jamaican test-takers generally found topics such as measurement; and function, relations, and graphs more difficult in comparison to other topics. They displayed more of their misunderstandings or misconceptions in specific concepts tested in these areas on the test. The findings from this study have implications for the teaching and learning of mathematics in Jamaica before, at, and after the CSEC level.