The purpose of this study is to analyze items that exhibit gender-related Differential Item Functioning (DIF) in Mathematics in Jordan. Data was taken from the TIMSS 1999 of Jordan, which includes responses of 5, 299 eighth grade students. Mantel-Haenszel (MH) DIF procedure was applied to 124 multiple-choice items. The results showed that 37 items exhibited gender-related DIE. The analysis of the content of these items reflected some patterns that need further investigation. All the DIF items in measurement content favored male students while most of the DIF items in algebraic and data analysis contents favored female students. Most of the DIF items that negatively impacted on females were unfamiliar items that required some risk taking such as estimation, expectation, or approximation. On the other hand, most of the DIF items that favored females were familiar items which have one specific correct answer. Some implications for both research and teaching practice are provided. (Contains 4 tables and 1 figure.)