Purpose: Addressing trapezio-metacarpal (TMC) osteoarthritis often involves considering TMC joint replacement. Utilizing TMC prostheses offers advantages such as preserving the thumb length and more accurately replicating the thumb’s range of motion (ROM). TMC prostheses have an intrinsic risk of dislocation and aseptic loosening. Analyzing pre- and postoperative imaging can mitigate complications and improve prosthetic placement, providing insights into both successes and potential challenges, refining overall clinical outcomes. Materials and methods: We conducted a prospective analysis of 30 patients with severe TMC arthritis treated with a Touch© (Kerimedical, Geneva, Switzerland) prosthesis in 2021–2023: X-ray and CT protocols were developed to analyze A) the correct prosthesis placement and B) its correlation with clinical outcomes (VAS, Kapandji and QuickDASH scores) by performing Spearman correlation analysis. Results: The average differences in trapezium height and M1-M2 ratio pre- and post-surgery were, respectively, 1.8 mm (SD ± 1.7; p < 0.001) and 0.04 mm (SD ± 0.04; p = 0.017). Pre-to-postoperative M1 axis length increased by an average of 2.98 mm (SD ± 3.84; p = 0.017). Trapezial cup sinking, indicated by the trapezium index, measured 4.6 mm (SD ± 1.2). The metacarpal index averaged at 11.3 mm (SD ± 3.3). The distance between the centers of the trapezium distal surface and the prosthesis cup was 2.23 mm (SD ± 1.4). The Spearman correlation analysis gave the following results: negative correlations were highlighted between postoperative VAS scores and the M1/M2 ratio and residual trapezium height (correlation coefficient: −0.7, p = 0.03 and −0.064, p = 0.03, respectively) at 6 months; a negative correlation was found at the 3-month mark between QuickDASH and the trapezium residual height (correlation coefficient: −0.07, p = 0.01); and a positive correlation was found for the trapezium index at 1 month (correlation coefficient: 0.07, p = 0.03) and 3 months (p = 0.04) using the Kapandji score. Similarly, we found a positive correlation between the distance between the prosthesis and trapezium centers and QuickDASH score at 1 and 3 months (correlation coefficient: 0.066, p = 0.03; correlation coefficient: 0.07, p = 0.05, respectively) and a positive correlation between prosthesis axis and the residual first metacarpal angle with QuickDASH score at 3 months (correlation coefficient: 0.07, p = 0.02). Conclusions: Pre- and postoperative systematic imaging analysis should become a method for predicting complications and guiding recovery in TMC prosthesis: CT imaging could provide us with radiographical landmarks that are intrinsically linked to clinical outcomes. Further research is necessary to fuel a protocol for the correct intraoperative TMC prosthesis implantation.