Well-being or quality of life is thought to give a more accurate picture of the impact a condition has on day-to-day functioning than traditional outcome measures. This study sought to examine the relationship between engagement in play and well-being for preschool children with and without developmental coordination disorder (DCD). A quasi-experimental design was used with two independent groups of preschool children aged 4–6 years with (n = 32) and without (n = 31) probable DCD. Play skills were assessed using the Play Observation Scale based on 30 min of videotape of free-play at preschool. Well-being was assessed using a parent-proxy version of the Revised Children Quality of Life Questionnaire (KINDLR). Spearman rho correlations were performed to examine the relationship between play and well-being. Well-being at preschool was significantly lower for the children in the DCD group however overall well-being was not significantly different. Engagement in type of social play (solitary, parallel or group) was found to predict well-being for the typically developing children. For the children with DCD, engagement in group play was not associated with well-being. An explanation for this difference may be that children with DCD may not experience free-play at preschool as “play” but rather as hard work. Further research is needed to determine why children with DCD experience lower well-being at preschool than their peers and to investigate children's perceptions of free-play. This may enable teachers and therapists to better support children with DCD in the preschool environment.