Indirect tests of memory associations relevant to cannabis have been shown to be useful in explaining and predicting adolescent cannabis use habits. This study sought to increase the understanding of adolescent cannabis-related associative memory and cannabis use behavior over time. A longitudinal sample of alternative high school students (N = 775) was assessed yearly for 3 years. The study first conducted extensive longitudinal measurement analyses of the cannabis-related word association test (WAT) applying contemporary psychometric models. Second, the study examined the longitudinal trajectories of cannabis-related associative memory and cannabis use and their contemporaneous and longitudinal relationships. Results showed that the cannabis-related WAT provided strong evidence of sound psychometric properties. Longitudinal change in cannabis-related associative memory was best described by modeling either a linearly decreasing trajectory or two separate trajectories: During middle adolescence, levels of cannabis-related associative memory were highest and stable but then gradually decreased toward late adolescence. Moreover, cannabis-related associative memory was contemporaneously predictive of cannabis use within ages 15 to 19 while controlling for the underlying growth process of cannabis use and time-invariant covariates (TICs) of gender and lifetime concurrent use of alcohol and cigarettes. Partial support of longitudinal prediction of cannabis use was also obtained from age 17 to 18 and age 19 to 20 while adjusting for growth in cannabis use and the TICs. These results demonstrated that predictive effects of cannabis-related memory associations on cannabis use were detected within some of the 1-year age spans and were consistent within ages across adolescent years.