The purpose of this paper is to present data demonstrating the differential pattern of association among play behaviors and developmental age that emerge for children with and without mental retardation across play situations. Seventeen preschool children with mental retardation and 17 preschool children without mental retardation were matched on developmental age and sex and observed during both home-based independent play and classroom-based freeplay. Results are presented for (a) between-group comparisons of home-based and classroom-based categorical-developmental age and sequential play-developmental age correlational patterns, (b) between setting comparisons of home-based and classroom-based categorical-developmental age and sequential play-developmental age correlational patterns within each group, and (c) comparisons of the pattern of categorical play-developmental age and sequential play-developmental age correlations within both setting and group. Results suggest both group and setting variation in the play-developmental age correlational patterns. Implications for multi-contextual understanding of children's play and the use of play in early childhood assessment are discussed.