More and more researchers are considering the omnibus eye movement sequence—the scanpath—in their studies of visual and cognitive processing (e.g. Hayes, Petrov, & Sederberg, 2011; Madsen, Larson, Loschky, & Rebello, 2012; Ni et al., 2011; von der Malsburg & Vasishth, 2011). However, it remains unclear how recent methods for comparing scanpaths perform in experiments producing variable scanpaths, and whether these methods supplement more traditional analyses of individual oculomotor statistics. We address this problem for MultiMatch (Jarodzka et al., 2010; Dewhurst et al., 2012), evaluating its performance with a visual search-like task in which participants must fixate a series of target numbers in a prescribed order. This task should produce predictable sequences of fixations and thus provide a testing ground for scanpath measures. Task difficulty was manipulated by making the targets more or less visible through changes in font and the presence of distractors or visual noise. These changes in task demands led to slower search and more fixations. Importantly, they also resulted in a reduction in the between-subjects scanpath similarity, demonstrating that participants’ gaze patterns became more heterogenous in terms of saccade length and angle, and fixation position. This implies a divergent strategy or random component to eye-movement behaviour which increases as the task becomes more difficult. Interestingly, the duration of fixations along aligned vectors showed the opposite pattern, becoming more similar between observers in 2 of the 3 difficulty manipulations. This provides important information for vision scientists who may wish to use scanpath metrics to quantify variations in gaze across a spectrum of perceptual and cognitive tasks.