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.