Children’s physical activity levels are higher at the start of outdoor playtime, which suggests that shorter, more frequent play periods might result in greater amounts of daily physical activity. In this extension of the Supporting Physical Activity in the Childcare Environment (SPACE) cluster randomized controlled trial, we explored the impact of four 30-min daily outdoor unstructured play periods on preschoolers’ moderate-to-vigorous-intensity physical activity (MVPA). Experimental childcare centres (n = 6) implemented four 30-min daily outdoor playtimes for 8 weeks, while control centres (n = 6) maintained their two 60-min outdoor sessions. Actical™ accelerometers were used to measure preschoolers’ physical activity pre- and post-intervention for 5 days during childcare hours. Linear mixed effects models were used to determine the impact of the intervention on preschoolers’ MVPA. Of the 185 preschoolers enrolled (54.20% female; mean age = 39.90 months, SD = 7.24), 127 (65 experimental and 62 control) were included in the analysis (30% and 9% loss to follow-up for experimental and control group preschoolers, respectively). No significant differences in MVPA were observed between groups over time (p = 0.36). Preschoolers’ MVPA did not improve after the introduction of shorter outdoor play periods. The loss of data due to wear time noncompliance and participant attrition may have influenced these findings. Trial registration: ISRCTN70604107 (October 8, 2014).