Dietary habits are considered a leading behavioral risk factor for human health. There is growing scientific evidence suggesting that diet and sleep may be related. The aim of this study was to review the evidence of association between diet and sleep quality. A systematic search in electronic databases PubMed, Embase, Scopus, and the Cochrane Central Register of Controlled Trials was conducted from their inception to November 2019. Studies investigating parameters of diet quality (including dietary patterns or individual healthy/unhealthy foods) and sleep quality (assessed through self-reported or objective methods) were included. The NIH Quality Assessment Tools were used to evaluate the study quality. Twenty-nine studies were reviewed: in summary, consumption of healthy foods was associated with better sleep quality, while higher intake of processed and free-sugar rich foods was associated with worse sleep features. Despite a certain consistency between studies have been observed, the overall poor-to-fair quality of study design (mostly represented by cross-sectional investigations) does not allow to conclude a causal relation. However, diet-related variables are associated with sleep quality, but further studies are needed to corroborate this finding.