(1) Background: Stent underexpansion is the main cause of stent thrombosis and restenosis. Coronary angiography has limitations in the assessment of stent expansion. Enhanced stent imaging (ESI) methods allow a detailed visualization of stent deployment. We qualitatively compare image results from two ESI system vendors (StentBoost™ (SB) and CAAS StentEnhancer™ (SE)) and report quantitative results of deployed stents diameters by quantitative coronary angiography (QCA) and by SE. (2) Methods: The ESI systems from SB and SE were compared and graded by two blinded observers for different characteristics: 1 visualization of the proximal and distal edges of the stents; 2 visualization of the stent struts; 3 presence of underexpansion and 4 calcifications. Stent diameters were quantitatively measured using dedicated QCA and SE software and compared to chart diameters according to the pressure of implantation. (3) Results: A total of 249 ESI sequences were qualitatively compared. Inter-observer variability was noted for strut visibility and total scores. Inter-observer agreement was found for the assessment of proximal stent edge and stent underexpansion. The predicted chart diameters were 0.31 ± 0.30 mm larger than SE diameters (p < 0.05). Stent diameters by SE after post-dilatation were 0.47 ± 0.31 mm smaller than the post-dilation balloon diameter (p < 0.05). SE-derived diameters significantly differed from QCA; by Bland–Altman analysis the bias was −0.37 ± 0.42 mm (p < 0.001). (4) Conclusions: SE provides an enhanced visualization and allows precise quantitative assessment of stent expansion without the limitations of QCA when overlapping coronary side branches are present.