Health policy makers worldwide have adopted evidence-based legislation, largely directed at consumers, to reduce tobacco-related harm. It is suggested that limiting supply by decreasing retail availability can also reduce cigarette smoking. To inform policy makers this systematic literature review assesses whether reducing availability is associated with smoking behaviours. Systematic literature searches of five databases were carried out up to January 2023. Included studies had at least one exposure (tobacco retail density, proximity or mixed measures thereof) and outcomes of smoking behaviour. Meta-analysis of effect estimates were undertaken if there were at least three studies with similar population, exposure and outcome measures. Sixty-two studies were included, and positive associations were found between tobacco outlet density and cigarette smoking in pregnancy, youth, adults and cessation. Meta-analyses were undertaken for retail density and ever smoking (odds ratio [OR] 1.20; 95% confidence interval [CI] 1.04, 1.37; I2 = 87.3%), and current youth smoking (OR 1.23; 95% CI 1.08, 1.40; I2 = 0.0%), adult smoking (OR 1.11; 95% CI 1.01, 1.22; I2 = 74.8%); and mixed measures of retail availability near schools and current youth smoking (OR 1.03; 95% CI 1.01, 1.05; I2 = 0.0%). There is evidence higher tobacco retail density is consistently associated with cigarette smoking in pregnant women, young people and adults when ecological studies are included in meta-analysis. Meanwhile, evidence synthesis reveals restrictive tobacco retail laws based on proximity or mixed measures near home or very near school may not reduce smoking except in men who smoke heavily. Mechanisms to reduce retailer density should be thus considered part of tobacco control strategies.