PURPOSE: The aim of this study is to determine the perceived familiarity of medical residents with statistical concepts, assess their ability to integrate these concepts in clinical scenarios, and investigate their susceptibility to the gambler's fallacy and the conjunction fallacy. METHODS: A multi-institutional, cross-sectional survey of Greek medical residents was performed. Participants were asked to indicate their familiarity with basic statistical concepts and answer clinically oriented questions designed to assess their biostatistics knowledge and cognitive biases. Univariate, bivariate, and multivariate statistical models were used for the evaluation of data. RESULTS: Out of 153 respondents (76.5% response rate), only two participants (1.3%) were able to answer all seven biostatistics knowledge questions correctly while 29 residents (19%) gave incorrect answers to all questions. The proportion of correct answers to each biostatistics knowledge question ranged from 15 to 51.6%. Residents with greater self-reported familiarity were more likely to perform better on the respective knowledge question (all p<0.01). Multivariate analysis of the effect of individual resident characteristics on questionnaire performance showed that previous education outside Greece, primarily during medical school, was associated with lower biostatistics knowledge scores (p<0.001). A little more than half of the respondents (54.2%) answered the gambler's fallacy quiz correctly. Residents with higher performance on the biostatistics knowledge questions were less prone to the gambler's fallacy (odds ratio 1.38, 95% confidence intervals 1.12-1.70, p=0.003). Only 48 residents (31.4%) did not violate the conjunction rule. CONCLUSIONS: A large number of medical residents are unable to correctly interpret crucial statistical concepts that are commonly found in the medical literature. They are also especially prone to the gambler's fallacy bias, which may undermine clinical judgment and medical decision making. Formalized systematic teaching of biostatistics during residency will be required to de-bias residents and ensure that they are proficient in understanding and communicating statistical information.