Background and Objectives: This longitudinal study investigated the correlation between imaging findings and self-reported questionnaire outcomes in patients with tibiofibular diastasis, exploring the effects of surgical screw removal versus conservative treatment. This study was conducted at “Victor Babes” University of Medicine and Pharmacy in Timisoara between 2018 and 2023. Materials and Methods: The study involved 85 patients in the screw removal group and 44 in the conservative group, assessed at 2 and 6 months post-surgery, answering the SF-36, HADS, and WHOQOL questionnaires. Results: Significant differences were observed at 2 months post-surgery, with the screw removal group showing lower shear wave velocities in ankle dorsiflexion (8.9 ± 1.4) and anterior talofibular ligament (2.8 ± 0.9), indicating better mobility compared to the conservative group (ankle dorsiflexion: 10.1 ± 1.8, ATFL: 3.2 ± 1.1). Radiographically, lower tibiofibular overlap (8.1 ± 2.1) in the screw removal group suggested improved joint fixation quality. These physical improvements were mirrored in the quality-of-life assessments, where the screw removal group reported higher physical health scores on the SF-36 survey at 2 months, a trend that continued at 6 months. At 2 months, ankle dorsiflexion demonstrated a strong negative correlation with the SF-36 Physical score (r = −0.417) and WHOQOL Physical domain (r = −0.394), and a positive correlation with HADS Anxiety (r = 0.312). Similarly, ATFL and CFL velocities negatively correlated with the SF-36 Physical score (ATFL: r = −0.251; CFL: r = −0.237). Radiographic tibiofibular overlap and clear space positively correlated with WHOQOL Physical domain (TOL: r = 0.291; TCS: r = 0.276), with TCS also negatively correlating with HADS Anxiety (r = −0.228). At 6 months, these correlations persisted, with notable negative correlations between ultrasound ankle dorsiflexion and both SF-36 Physical score and WHOQOL Physical domain. Conclusions: These findings underscore the advantages of screw removal in enhancing physical recovery and reducing anxiety in the short term, while indicating similar long-term mental health outcomes between treatment approaches.