Studies of the benefits of a distributed practice schedule on motor skill acquisition have typically found that distribution of practice results in better learning. However, less research has focused on how the benefits of distributed practice are impacted by timing during acquisition. To examine how timing of skill acquisition interacts with distribution of practice we had two groups of participants complete either an extensive massed or distributed training schedule to learn a speed stacking sequence across ten sessions. For participants in both groups, we provided observational learning to facilitate skill acquisition. Analysis of speed stacking time on a retention test revealed an overall benefit for the distributed relative to the massed practice group. Interestingly, our analysis of the benefits of distributed practice during training only showed performance benefits in the early session (session one) and later sessions (sessions eight, nine, and ten) of skill acquisition but not mid-way through it (sessions two through seven). Our results support previous findings highlighting the learning benefits of a distributed practice schedule but suggest that these benefits occur differentially throughout acquisition. Our work also replicates research demonstrating that observational learning is more beneficial when it is yoked to actual practice.