This study examines similarities and differences in teacher ratings of behavioral problems and adaptive skills between a sample of 320 students from Anguilla, BWI and 315 children from the United States of America using the Behavior Assessment System for Children (BASC; Reynolds & Kamphaus, 1992). The study also compared teacher ratings of boys and girls in the Caribbean sample. Analyses of variance (ANOVA) revealed that Anguillian teachers rated their students as having higher mean school problems, while the mean score for adaptive skills was higher for US students. Effect sizes were small, though, indicating that little of the variance in ratings was attributable to cultural group. Boys in the Caribbean sample had significantly higher mean scores on externalizing and school problems. Girls were rated at having more adaptive skills. Again, effect sizes for the differences were small. Scientific and practice implications are offered.