Researchers have documented how athletes navigate transitions within high-performance sport; however, little is known about the transitions that youth athletes face in their athletic development. When studying youth sport populations, it is imperative to consider how sports experiences coincide with children’s changing psychosocial abilities. The purpose of this study was to explore how children’s psychosocial abilities interact with their sports participation as they attempt to navigate the transition from recreational to competitive sport. Seven children (Mage = 10 years, 6 females, 1 male) and their parents participated in a mixed methods study. Parents and children completed qualitative interviews and measures of the child’s perceived social and athletic competencies (Harter, 1985) at three time points across a 12-month period. Qualitative data were analyzed using reflexive thematic analysis, and quantitative data were integrated throughout the results. Each dyad had a unique transitional experience; some children transitioned into more competitive levels of sport, while others needed multiple attempts to qualify for new teams (i.e., multiple tryouts over 12 months), and other children did not transition into more competitive sport levels. Salient transition experiences, such as tryouts or meeting new teammates, presented children with opportunities to demonstrate psychosocial abilities such as social comparisons and self-evaluations with peers. Challenges for sports clubs due to the COVID-19 pandemic impacted children’s opportunities to transition in sport. This study provides initial insight into how young athletes and parents perceive and experience phases of their sport transition, and how children’s psychosocial abilities can play a role in the transition process.