Discrepancies in cross informant reports of social, emotional and behavioral difficulties in children are common. These discrepancies may not represent the lack of validity of a single informants report and should be examined as additional informative data when completing a comprehensive evaluation of a child. Potential factors that influence the correspondence (correlations) and discrepancies (mean differences) between informant’s ratings provide additional data that may influence the overall understanding of the child’s functioning and the determination of appropriate treatment considerations. This study investigated the correspondence and discrepancies between 302 child, caregiver, and teacher reports of behavioral and emotional strengths and difficulties utilizing the Strengths and Difficulties Questionnaire (SDQ). Grade level, gender and relational aspects were explored as potential moderators influencing agreement between raters. The Student Teacher Relationship Scale (STRS) and the Child Parent Relationship Scale (CPRS) were utilized to examine parent-child and teacher-child relational aspects. Results were consistent with the literature reporting low to moderate correspondence between student, parents and teachers ratings on the SDQ. Although students endorsed higher levels of Total Difficulties than parents and caregivers, teacher’s rated overall higher levels of externalizing and internalizing difficulties than parents and students. Gender influenced agreement on internalizing symptoms, but grade level was less consistent as a potential moderator. Parent-child and teacher-student relationships influenced agreement on Peer Problems, Hyperactivity and Pro Social Skills. Interestingly, student’s whose teacher’s reported ‘Not Close’ or ‘High Conflict’ relationships endorsed higher levels of internalizing difficulties.