Preschool aged children are encouraged to accumulate at least three hours of physical activity (PA) daily (CSEP, 2012), yet there are contradictory reports as to how many preschoolers are meeting these recommendations (AHKC, 2010; CFLRI, 2015). Further, 35% of children in this age group are classified as overweight or obese (Shields &Tremblay, 2010). While many experts suggest free play as an optimal means for preschoolers to attain recommended PA levels (ParticipACTION Report Card, 2015), an interesting paradox is that organized preschool sport programs appear to be growing in popularity. The purpose of this study was to examine proposed developmental outcomes of preschooler sport programs in Toronto. Data was collection through two approaches: a) a systematic Google web search resulted in 90 programs of common organized preschooler sport activities (i.e., soccer, baseball, gymnastics, skating, martial arts, Fraser-Thomas & Safai, in press), and b) a systematic search through the Toronto Fun Guide (City of Toronto, 2016). Content analysis results suggest sport programmers claim extensive physical and psychosocial benefits for preschoolers. Preliminary results show some differences according to sport type (e.g., martial arts cite more psychosocial benefits than other sport types), and program type (e.g., greater promotion of benefits by for profit programs than by City of Toronto programs). The disconnect between proposed developmental outcomes and limited supporting research is discussed. Accordingly, future research is recommended to investigate if and how preschoolers may gain developmental benefits through organized sport.