This study explores the visual strategies of University Supervisor Trainers (UST) for teachers [Upper Secondary Education Teaching Certification—Agrégation de l’Enseignement Secondaire Supérieur (AESS)] in French-speaking Belgium and the pre-service teachers (PT) they train. It aims to understand how these two groups observe a teaching situation, on video, using an eye-tracking device. The video shows the start of a geography lesson given by a trainee in a primary school class. Three research questions were formulated, examining (a) the actor observed (the trainee, the pupil working groups and 4 pupil profiles present in the scene), (b) the visual strategies used to access these actors, and (c) the visual itineraries when a planning error by the trainee is presented on the screen. To answer, we chose to carry out an analysis based on oculometric indicators (fixing, visit, and first view). The results show that UST and PT focus their attention on the same groups of students. However, they do not do so in the same way. UST adopt visual strategies that are distinct from those of PT, thus aligning their approaches with those of expert teachers in other studies using eye tracking. Within these strategies, we highlight two important points: (a) the emergence of dynamic and floating visual strategies in the UST, characterized by more frequent revisits (significantly validated) and fixations of shorter duration than in PT; and (b) less fixation of UST in observing students who are very active in class compared to PT. Finally, the specific analysis of the UST gaze itineraries at the time of the trainee’s planning error reflected both common elements (e.g., teaching tools) and divergent elements (e.g., checking pupils).