The Intelligibility in Context Scale (ICS) is a widely used, efficient tool for describing a child’s speech intelligibility. Few studies have explored the relationship between ICS scores and transcription intelligibility scores, which are the gold standard for clinical measurement. This study examined how well ICS composite scores predicted transcription intelligibility scores among children with cerebral palsy (CP), how well individual questions from the ICS differentially predicted transcription intelligibility scores, and how well the ICS composite scores differentiated between children with and without speech motor impairment. Parents of 48 children with CP, who were approximately 13 years of age, completed the ICS. Ninety-six adult naïve listeners provided orthographic transcriptions of children’s speech. Transcription intelligibility scores were regressed on ICS composite scores and individual item scores. Dysarthria status was regressed on ICS composite scores. Results indicated that ICS composite scores were moderately strong predictors of transcription intelligibility scores. One individual ICS item differentially predicted transcription intelligibility scores, and dysarthria severity influenced how well ICS composite scores differentiated between children with and without speech motor impairment. Findings suggest that the ICS has potential clinical utility for children with CP, especially when used with other objective measures of speech intelligibility.