(1) Background and aim: The effects of functional therapies on dentoalveolar and skeletal structures have been investigated in orthodontics for many years. The aim of this retrospective study was to evaluate the changes caused by fixed and removable functional therapy in the mandibular anterior trabecular structures using fractal dimension (FD) analysis. (2) Methods: A total of 60 patients with skeletal and dental class II malocclusion were included in the study and three groups were formed: the untreated control group (CG), the Forsus fatigue-resistant device group (FFRDG), and the Monoblock group (MBG). Bone areas of interest determined in the buccoapical of the mandibular incisors and the symphysis in the lateral cephalometric radiographs taken before (T0) and after (T1) functional therapy were evaluated using FD analysis. The relationship between the FD and IMPA (Incisor Mandibular Plane Angle) angles was evaluated. Parametric and nonparametric tests were used in statistical analysis according to normality distribution. The statistical significance level was determined as p < 0.05. (3) Results: There was no statistically significant difference between the FD values of all groups at T0 (p > 0.05). At T1, buccoapical FD values were significantly lower in FFRDG and MBG compared to the control group (p < 0.05), while symphyseal FD values were not found to be significant (p > 0.05). The IMPA angle was significantly lower in the FFRDG and MBG than in the control group at T0, while it was higher at T1 (p < 0.05). While a significant negative correlation was observed between the IMPA angle and buccoapical FD values in both FFRDG and MBG (p < 0.05), it was not observed with the symphysis FD values (p > 0.05). (4) Conclusions: Trabecular changes caused by functional therapy in the mandibular anterior bone can be evaluated on lateral cephalometric radiographs with FD analysis. It was concluded that orthodontists should ensure controlled changes in the IMPA angle during functional therapy, especially for the decreases in FDs seen in the buccoapical alveolar region due to the forward movement of the mandibular incisors.