(1) Background: Analyses of retrieved inserts allow for a better understanding of TKA failure mechanisms and the detection of factors that cause increased wear. The purpose of this implant retrieval study was to identify whether insert volumetric wear significantly differs among groups of common causes of total knee arthroplasty failure, whether there is a characteristic wear distribution pattern for a common cause of failure, and whether nominal insert size and component size ratio (femur-to-insert) influence linear and volumetric wear rates. (2) Methods: We digitally reconstructed 59 retrieved single-model cruciate-retaining inserts and computed their articular load-bearing surface wear utilizing an optical scanner and computer-aided design models as references. After comprehensively reviewing all cases, each was categorized into one or more of the following groups: prosthetic joint infection, osteolysis, clinical loosening of the component, joint malalignment or component malposition, instability, and other isolated causes. The associations between volumetric wear and causes of failure were estimated using a multiple linear regression model adjusted for time in situ. Insert linear penetration wear maps from the respective groups of failure were further processed and merged to create a single average binary image, highlighting a potential wear distribution pattern. The differences in wear rates according to nominal insert size (small vs. medium vs. large) and component size ratio (≤1 vs. >1) were tested using the Kruskal-Wallis test and the Mann-Whitney test, respectively. (3) Results: Patients with identified osteolysis alone and those also with clinical loosening of the component had significantly higher volumetric wear when compared to those without both causes (p = 0.016 and p = 0.009, respectively). All other causes were not significantly associated with volumetric wear. The instability group differentiated from the others with a combined peripheral antero-posterior wear distribution. Linear and volumetric wear rates showed no significant differences when compared by nominal insert size (small vs. medium vs. large, p = 0.563 and p = 0.747, respectively) or by component (femoral-to-insert) size ratio (≤1 vs. >1, p = 0.885 and p = 0.055, respectively). (4) Conclusions: The study found increased volumetric wear in cases of osteolysis alone, with greater wear when combined with clinical loosening compared to other groups. The instability group demonstrated a characteristic peripheral anterior and posterior wear pattern. Insert size and component size ratio seem not to influence wear rates.