Despite the emerging literature supporting the central role of pretend play for children’s cognitive, affective and social development, there is a paucity of standardized and validated measures devoted to assess it, especially for preschoolers. In addition, most of the existing tools failed in their attempt to assess the interplay among the different developmental domains which are involved in playing activities. The Affect in Play Scale-Preschool version is a semi-structured measure to assess cognitive and affective pretend play processes in children aged 4–5 using a 5-min standardized play task. This study was aimed to evaluate the construct and external validity of the scale in a sample of Italian preschoolers. A multi-group factor analysis confirmed the adequacy of the two-factor model with cognitive and affective factor for both 4- and 5-year-old children. No differences were found between boys and girls whereas older children reported higher play abilities. Correlations between pretend play, divergent thinking, teacher’s measures of temperament and prosocial behavior were carried out. Results supported the use of APS-P as a valid tool for assessing the interplay of cognitive and affective abilities in Italian children.