The current study investigated the association between Machiavellianism and children’s peer interactions in the playground using observational methods. Primary school children (N = 34; 17 female), aged 9 to 11 years, completed the Kiddie Mach scale and were observed in natural play during 39 recesses (average observed time = 11.70 hours) over a full school year. Correlations for boys revealed that Machiavellianism was related to more time engaging in direct and indirect aggression, being accepted into other peer groups, and accepting peers into their own social group. Correlations revealed that for girls, Machiavellianism was associated with lower levels of indirect aggression, less time being accepted into other groups and less time accepting and rejecting other children into their own group. This preliminary pilot study indicates that Machiavellianism is associated with children’s observed social behaviour and aims to promote future observational research in this area.