BACKGROUND: In recent years, there have been numerous studies exploring different teaching methods for improving diagnostic reasoning in undergraduate medical students. This systematic review examines and summarizes the evidence for the effectiveness of these teaching methods during clinical training. METHODS: PubMed, Embase, Scopus, and ERIC were searched. The inclusion criteria for the review consist of articles describing (1) methods to enhance diagnostic reasoning, (2) in a clinical setting (3) on medical students. Articles describing original research using qualitative, quantitative, or mixed study designs and published within the last 10 years (1 April 2009–2019) were included. Results were screened and evaluated for eligibility. Relevant data were then extracted from the studies that met the inclusion criteria. RESULTS: Sixty-seven full-text articles were first identified. Seventeen articles were included in this review. There were 13 randomized controlled studies and four quasi-experimental studies. Of the randomized controlled studies, six discussed structured reflection, four self-explanation, and three prompts for generating differential diagnoses. Of the remaining four studies, two employed the SNAPPS(1) technique for case presentation. Two other studies explored schema-based instruction and using illness scripts. Twelve out of 17 studies reported improvement in clinical reasoning after the intervention. All studies ranked level two on the New World Kirkpatrick model. DISCUSSION: The authors posit a framework to teach diagnostic reasoning in the clinical setting. The framework targets specific deficiencies in the students’ reasoning process. There remains a lack of studies comparing the effectiveness of different methods. More comparative studies with standardized assessment and evaluation of long-term effectiveness of these methods are recommended. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s11606-021-06916-0.