Background: Numerous diagnostic imaging measurements related to patellar instability have been evaluated in the literature; however, little has been done to compare these findings across multiple studies. Purpose: To review the different imaging measurements used to evaluate patellar instability and to assess the prevalence of each measure and its utility in predicting instability. We focused on reliability across imaging modalities and between patients with and without patellar instability. Study Design: Systematic review; Level of evidence, 4. Methods: We performed a systematic review of the literature using the PubMed, SCOPUS, and Cochrane databases. Each database was searched for variations of the terms “patellar instability,” “patellar dislocation,” “trochlear dysplasia,” “radiographic measures,” “computed tomography,” and “magnetic resonance imaging.” Studies were included if they were published after May 1, 2009, and before May 1, 2019. A meta-analysis using a random effects model was performed on several measurements, comparing instability and control groups to generate pooled values. Results: A total of 813 articles were identified, and 96 articles comprising 7912 patients and 106 unique metrics were included in the analysis. The mean patient age was 23.1 years (95% CI, 21.1-24.5), and 41% were male. The tibial tubercle–trochlear groove (TT-TG) distance was the most frequently included metric (59 studies), followed by the Insall-Salvati ratio and Caton-Deschamps index (both 26 studies). The interobserver intraclass correlation coefficients were excellent or good for the TT-TG distance and Insall-Salvati ratio in 100% of studies reporting them; however, for the Caton-Deschamps index and Blackburne-Peel ratio, they were excellent or good in only 43% and 40% of studies. Pooled magnetic resonance imaging values for TT-TG distance ( P < .01), Insall-Salvati ratio ( P = .01), and femoral sulcus angle ( P = .02) were significantly different between the instability and control groups. Values for tibial tubercle–posterior cruciate ligament distance ( P = .36) and Caton-Deschamps index ( P = .09) were not significantly different between groups. Conclusion: The most commonly reported measurements for evaluating patellar instability assessed patellar tracking and trochlear morphology. The TT-TG distance was the most common measurement and was greater in the patellar instability group as compared with the control group. In addition, the TT-TG, tibial tubercle–posterior cruciate ligament, and patellar tendon–trochlear groove distances were highly reproducible measurements for patellar tracking, and the Insall-Salvati ratio had superior reproducibility for assessing patellar height.