Children who sustain a traumatic brain injury frequently present with linguistic deficits that persist into adulthood. Relatively little is known, however, about the listening comprehension abilities of these children in their adolescent years. Secondary school education places heavy demands on listening comprehension and impairment at this level is likely to negatively impact upon academic achievement and the development of peer relationships. The present study investigated the listening comprehension performance of adolescents who suffered a traumatic brain injury (TBI) during childhood and explored factors that may influence their comprehension of advanced language forms. Listening comprehension was examined in this study from a perspective of typical language development in adolescence as well as from a working memory theory of listening comprehension. Six adolescents with TBI and six age-matched controls, as well as a typically developing group of adolescents participated in the study. Following the establishment of normative estimates for New Zealand adolescents on measures of working memory, a battery of standardized language and memory tests were administered to examine the listening comprehension and working memory profiles in the six adolescents with TBI. A series of experiments was then conducted to further explore the performance of adolescents with TBI in comprehending proverbs, idioms, and inferences and to explore the influence of working memory demands of the tasks on comprehension performance. Results revealed that the adolescents with TBI presented with listening comprehension impairment relative to their age-matched peers. Adolescents with TBI were, however, significantly more sensitive to increased working memory demands of comprehension tasks compared to their peers, performing better on tasks that required low working memory storage and processing demands. A working memory theory for explaining the deficits in TBI was posited. Theoretical and practical implications of the findings regarding working memory and language comprehension were discussed.