Background/Objectives: A popliteal artery aneurysm (PAA) is traditionally treated by an open PAA repair (OPAR) with a popliteo–popliteal venous graft interposition. Although excellent outcomes have been reported in elective cases, the results are much worse in cases of emergency presentation or with the necessity of adjunct procedures. This study aimed to identify the risk factors that might decrease amputation-free survival (efficacy endpoint) and lower graft patency (technical endpoint). Patients and Methods: A dual-center retrospective analysis was performed from 2000 to 2021 covering all consecutive PAA repairs stratified for elective vs. emergency repair, considering the patient (i.e., age and comorbidities), PAA (i.e., diameter and tibial runoff vessels), and procedural characteristics (i.e., procedure time, material, and bypass configuration). Descriptive, univariate, and multivariate statistics were used. Results: In 316 patients (69.8 ± 10.5 years), 395 PAAs (mean diameter 31.9 ± 12.9 mm) were operated, 67 as an emergency procedure (6× rupture; 93.8% severe acute limb ischemia). The majority had OPAR (366 procedures). Emergency patients had worse pre- and postoperative tibial runoff, longer procedure times, and more complex reconstructions harboring a variety of adjunct procedures as well as more medical and surgical complications (all p < 0.001). Overall, the in-hospital major amputation rate and mortality rate were 3.6% and 0.8%, respectively. The median follow-up was 49 months. Five-year primary and secondary patency rates were 80% and 94.7%. Patency for venous grafts outperformed alloplastic and composite reconstructions (p < 0.001), but prolonged the average procedure time by 51.4 (24.3–78.6) min (p < 0.001). Amputation-free survival was significantly better after elective procedures (p < 0.001), but only during the early (in-hospital) phase. An increase in patient age and any medical complications were significant negative predictors, regardless of the aneurysm size. Conclusions: A popliteo–popliteal vein interposition remains the gold standard for treatment despite a probably longer procedure time for both elective and emergency PAA repairs. To determine the most effective treatment strategies for older and probably frailer patients, factors such as the aneurysm size and the patient’s overall condition should be considered.