We investigated whether cattle exhibit preferences to monitor challenging and novel stimuli. Experiments were conducted on dairy and beef cattle herds and revealed significant left eye preferences in the cattle for viewing an experimenter walking to repeatedly split the herd through its centre. Visual lateralisation was demonstrated in the preference to use the left monocular field to monitor the experimenter, alone or equipped with a range of novel stimuli. This finding is consistent with left eye preferences found in various species of mammals, birds, and amphibians responding to predators and novel stimuli. A cohort of the familiarized cattle herds was then subjected to additional herd-splitting tests with the same stimuli and demonstrated a reversal of viewing preferences, preferring to monitor the experimenter and stimuli within the right and not left monocular field. This directional shift in viewing preferences is consistent with experience-dependent learning found in lateralised visual processing in other, non-mammalian, species, and to our knowledge is the first of such studies to suggest that such lateralised learning processes also exist in mammals. Together the data support a number of key hypotheses concerning the evolution and conservation of lateralised brain function in vertebrates, and also provide important considerations for livestock handling.