A cleft lip and/or palate (CL/P) is one of the most common craniofacial malformations, occurring worldwide in about one in 600–1000 newborn infants. CL/P is known to influence the feeding process negatively, causing feeding difficulties in 25–73% of all children with CL/P. Because there is a risk for serious complications in these children regarding feeding difficulties, there is often a need for intensive medical counseling and treatment. At this moment, adequate diagnosis and measurement remain a challenge and often lead to a delayed referral for professional help. Since parents play a big part in reporting feeding difficulties, it is important to help objectify parents’ experiences, as well as the use of a frontline screening instrument for routine check-ups during medical appointments. The aim of this study is to investigate the relationship between parent perspective and standardized observation by medical professionals on feeding difficulties in 60 children with and without clefts at the age of 17 months. We focus on the information from parents and health professionals by comparing the Observation List Spoon Feeding and the Schedule for Oral Motor Assessment with the validated Dutch translation of the Montreal Children’s Hospital Feeding Scale.Conclusion: There is a need for timely and adequate diagnosis and referral when it comes to feeding difficulties in children with CL/P. This study underscores the importance of combining both parental observations and measurements of oral motor skills by healthcare professionals to enable this.What is Known:•Early identification of feeding difficulties can prevent adversely affected growth and development.•Clefts increase the probability of feeding difficulties; however, the diagnostic trajectory is unclear.•The Observation List Spoon Feeding (OSF) and Schedule for Oral Motor Assessment (SOMA) are validated to measure oral motor skills. The Montreal Children’s Hospital Feeding Scale Dutch version (MCH-FSD) has been validated for the parental perception of infant feeding difficulties.What is New:•Parents of children with CL/P experience relatively few feeding problems in their child on average.•Oral motor skills for spoon feeding are associated with oral motor skills for solid foods in children with CL/P.•The extent of the cleft is associated with experiencing more feeding difficulties in children with CL/P.