AbstractListening can be conceptualized as a process of active inference, in which the brain forms internal models to integrate auditory information in a complex interaction of bottom-up and top-down processes. We propose that individuals vary in their “prediction tendency” and that this variation contributes to experiential differences in everyday listening situations and shapes the cortical processing of acoustic input such as speech. Here, we presented tone sequences of varying entropy level, to independently quantify auditory prediction tendency (as the tendency to anticipate low-level acoustic features) for each individual. This measure was then used to predict cortical speech tracking in a multi speaker listening task, where participants listened to audiobooks narrated by a target speaker in isolation or interfered by 1 or 2 distractors. Furthermore, semantic violations were introduced into the story, to also examine effects of word surprisal during speech processing. Our results show that cortical speech tracking is related to prediction tendency. In addition, we find interactions between prediction tendency and background noise as well as word surprisal in disparate brain regions. Our findings suggest that individual prediction tendencies are generalizable across different listening situations and may serve as a valuable element to explain interindividual differences in natural listening situations.