This paper focus mainly on gender differences in guessing tendencies in mathematics. Despite the inherent advantage of essay or free-response questions in terms of ease of construction, elimination of guessing and development of written skills, multiple choice item format is widely used because it leads to the development of objective assessment questions. Expost-facto survey design was used. A sample of 110 students (56 males and 54 females) was drawn through purposive sampling from selected schools in Delta North Senatorial District of Delta State. Final year (SS III) students of 2012/2013 academic session were used for the study. The 50-item objective test items in May/June, 2010 Mathematics administered by the West African Examination Council (WAEC) was the instrument used for the study. The paper concluded that there is no significant difference in the mean guessing score of male and female students in Mathematics.