Introduction Velopharyngeal insufficiency (VPI) and craniofacial differences can lead to diminished speech and swallowing function resulting in communication and social challenges throughout childhood. To monitor changes in patients' psychosocial health and velopharyngeal function, the Pediatric Symptom Checklist (PSC) and Velopharyngeal Insufficiency Effects on Life Outcomes (VELO) survey tools can be utilized. This study aimed to investigate the relationship between VPI quality-of-life outcomes and psychosocial disturbances through a comparative analysis of PSC and VELO parental surveys among children followed by a craniofacial team. Methods A retrospective chart review was completed using data from asingle, multidisciplinary cleft and craniofacial team. Previously completed parental survey responses between 2010 and 2022 were collated and resultswere analyzed using a Spearman's rank correlation test (rs). Results There were 89 subjects who completed both surveys on the same day (n = 148 survey pairs (s)). Patients aged three to five years old (s = 88) had a mean VELO of 17.9 (0-65) and a mean PSC of 7.9 (0-27), while patients aged six to eight years old (s = 60) had a mean VELO of 16.6 (0-74) and a mean PSC of 12.0 (0-37). The strongest correlation observed for both age groups was between the total PSC and VELO Speech Limitations sub-scores (three to five years old: rs = 0.537, p < 0.001; six to eight years old: rs = 0.330, p = 0.010). Similarly, children in the six- to eight-year-old group with cleft lip and palate showed a correlation between the total PSC and VELO Speech Limitations (rs = 0.583, p < 0.001). Conclusion This study suggests arelationship between PSC and VELO scores among childrenages three to eight years old with cleft differences and demonstrates that specific domains within theVELO questionnaireshould be considered as being associated with a higher riskfor psychosocial impairment. Specifically, higher VELO Speech Limitations sub-scores may portend a greater risk for poor psychosocial outcomes supporting the importance of early interventions in this group.