Adaptive hypermedia learning systems can be developed to adapt to a diversity of individual differences. Many studies have been conducted to design systems to adapt to learners’ individual characteristics, such as learning style and cognitive style to facilitate student learning. However, no research has been done specifically regarding the adaptation of hypermedia learning system to gender differences. This chapter therefore attempts to fill this gap by examining the published findings from experimental studies of interaction between gender differences and hypermedia learning. Analysis of findings of the empirical studies leads to a set of principles being proposed to guide adaptive hypermedia learning system design onthe basis of gender differences in relation to (i) adaptive presentation and (ii) adaptive navigation support.