This paper reports on an investigation on the real-life situations students in grades 8 and 9 in South Africa and Albania prefer to use in Mathematics. The functioning of the instrument used to assess the order of preference learners from both countries have for contextual situations is assessed using Rasch modeling techniques. For both the cohorts, the data fit the Rasch model. The differential item functioning (DIF) analysis rendered 3 items operating differentially for the two cohorts. Explanations for these differences are provided in terms of differences in experiences learners in the two countries have related to some of the contextual situations. Implications for interpretation of international comparative tests are offered, as are the possibilities for the cross-country development of curriculum materials related to contexts that learners prefer to use in Mathematics.