The contextual interference effect in motor learning refers to the interference that results from practising a task within the concept of other tasks in a practice session. Several studies have shown that practice under conditions of high contextual interference (i.e. with a random practice order) degrades performance during acquisition trials, compared to low contextual interference conditions (i.e. with a blocked order, where practice is completed on one task before practice on another task is undertaken). In contrast to acquisition performance, random practice usually leads to more effective learning than blocked practice, as measured by retention and transfer tests. One of the hypotheses regarding the effect suggests that a random practice schedule induces more extensive planning operations during practice than a blocked practice condition. If so, then differences between these two conditions should emerge to the degree that the set of tasks requires complete reconstruction of these planning operations on each trial. To address this issue, we compared four groups of subjects: a blocked and random group that practised three timing tasks that shared a common characteristic (same relative timing), and a blocked and random group that practised three tasks that each had different relative timing structures. Subjects practised these tasks on each of two days, with a retention test and two transfer tests that required either a relative timing structure that had been practised previously or had not previously been practised. No random/ blocked differences occurred regardless of the relative timing of the patterns during acquisition or retention. However, for both transfer tests, random practice enhanced learning only for the group that had practised with tasks that each had different relative timing during acquisition. Implications of these results for an explanation of contextual interference are discussed.