Word learning is an iterative and dynamic process supported by multiple neural and cognitive systems. Converging evidence from behavioral, cellular, and systems neuroscience highlights sleep as an important support for memory and word learning over time. In many lab-based word learning experiments, participants encode and subsequently retrieve newly learned words in a single session. These designs are inadequate to capture the full dynamic word learning process, making them less ecologically valid. Single timepoint studies also limit investigation of the role of behavioral and lifestyle factors, like sleep, in supporting word learning over time. Adults with a history of traumatic brain injury (TBI), who commonly exhibit deficits in the memory systems that support word learning and report concomitant sleep disturbance, provide a unique opportunity to examine the link between memory, sleep, and word learning. Here we examined word learning over time and the influence of sleep on short- and long-term word recall in 50 adults with chronic moderate-severe TBI and 50 demographically matched neurotypical peers. We used a randomized within-participant crossover design to assess immediate encoding of new words and the consolidation of those words over time across intervals that did or did not involve sleep. Participants completed this study over the course of two weeks in their own homes to capture the iterative, dynamic process of real-world word learning. We also measured sleep in free living conditions using actigraphy throughout the experiment. Participants with TBI exhibited a word learning deficit that began at encoding and persisted across time. Critically, this deficit grew over the course of the week. The performance gap between groups was larger at the 1-week post-test than the immediate post-test, suggesting deficits in both encoding and consolidation of new words in individuals with TBI. Participants with and without TBI remembered more words when they slept after learning. Ecologically valid research designs that examine the relationship between memory, sleep, and word learning over time promise to advance mechanistic accounts of word learning and improve the long-term retention of new words in individuals with and without brain injury.