The study investigated the psychometric properties of the West African Examinations Council (WAEC) May/June mathematics multiple choice items from 2019 to 2021 using classical test theory (CTT). Survey research design that adopted simple random sampling technique was used in selecting a sample of 2,484 senior secondary three (SS3) students from Owerri Education Zone 1 of Imo State. The study was guided by two research questions and two hypotheses. The instruments used were 2019, 2020 and 2021 WAEC mathematics multiple choice test items. The instruments (test items) were assumed to be valid and reliable by nature of standardized instrument administered by WAEC. The collected data were analyzed using jMetrik software in order to answer the research questions while ANOVA was used to test the hypotheses at α = 0.05 level of significance. Findings from the study showed that 43(86%) of the items in 2019, 41(82%) of the items in 2020 and 38(76%) of the items in 2021, satisfied the difficulty acceptable range. Again, 33(66%) of the items in 2019, 34(68%) of the items in 2020 and 32(64%) of the items in 2021 satisfied the acceptable discrimination range. The items had reasonable difficulty and discrimination levels. Based on the findings of this study, it was recommended that WAEC and other examination bodies should ensure that only quality items are developed for assessment.