Background: Mini dental implant (MDI) overdenture rehabilitation for the edentulous maxilla is a valuable, less invasive and affordable treatment alternative for complete removable dentures (CRD). However, comparative quantification of masticatory performance in different oral conditions are scarce. Purpose: This study compares objective masticatory performance of dentate groups, maxillary CRD and MDI overdentures and subjective masticatory performance in maxillary CRD and MDI overdentures. Materials and Methods: Four groups were defined, age 20+ dentate dental students (DS), age 50+ complete dentate subjects (DP), age 50+ maxillary CRD or MDI overdentures/dentate mandible. Objective masticatory performance was evaluated by measuring circular Variance of Hue (VOH) or the mixture degree of two-color chewing gum (Hue-check View Gum® Test). Additionally, subjective masticatory comparison was investigated in the CRD and MDI groups, with a visual analogue scale (VAS) for different food consistencies and the Oral Health Related Quality of Life (OHRQL) OHIP-14 questionnaire. Results: The mean VOH was 0.11 (SD 0.50, range 0.05–0.27) for the dentate dental 20+ students, 0.13 (SD 0.08, range 0.03–0.31) for the 50+ dentate group (p = 0.774), 0.41 (SD 0.41, range 0.14–0.76) for the CRD group and 0.39 (SD 0.18, range 0.07–0.76) for the MDI group (p = 0.725). Based on the VAS scores, no improvement was found between the CRD and the MDI overdenture group (p > 0.050). The mean OHIP-14 total score was 12.10 (SD 15.87, range 0–56) for CRD, while the MDI group (p = 0.039) saw a significant improvement to 2.85 (SD 2.85, range 0–15). Conclusion: Comparable results in objective masticatory performance were registered in dentate 20+ and 50+ subjects with a remarkable inferior outcome for the CRD and MDI group. Compared to CRD, MDI overdentures revealed no substantial improvement in subjective and objective masticatory performance. However, for MDI a significant increase in OHRQL was apparent.