Basic science and clinical studies suggest that sleep disturbance may be a modifiable risk factor for postoperative delirium. We aimed to assess the association between preoperative sleep disturbance and postoperative delirium. We searched PubMed, Embase, CINAHL, Web of Science, and Cochrane from inception until May 31, 2017. We performed a systematic search of the literature for all studies that reported on sleep disruption and postoperative delirium excluding cross-sectional studies, case reports, and studies not reported in English language. Two authors independently performed study selection and data extraction. We calculated pooled effects estimates with a random-effects model constructed in Stata and evaluated the risk of bias by formal testing (Stata Corp V.14, College Station, TX), DATA SYNTHESIS:: We included 12 studies, from 1,238 citations that met our inclusion criteria. The pooled odds ratio for the association between sleep disturbance and postoperative delirium was 5.24 (95% CI, 3.61-7.60; p < 0.001 and I = 0.0%; p = 0.76). The pooled risk ratio for the association between sleep disturbance and postoperative delirium in prospective studies (n = 6) was 2.90 (95% CI, 2.28-3.69; p < 0.001 and I = 0.0%; p = 0.89). The odds ratio associated with obstructive sleep apnea and unspecified types of sleep disorder were 4.75 (95% CI, 2.65-8.54; p < 0.001 and I = 0.0%; p = 0.85) and 5.60 (95% CI, 3.46-9.07; p < 0.001 and I = 0.0%; p = 0.41), respectively. We performed Begg's and Egger's tests for publication bias and confirmed a null result for publication bias (p = 0.371 and 0.103, respectively). Preexisting sleep disturbances are likely associated with postoperative delirium. Whether system-level initiatives targeting patients with preoperative sleep disturbance may help reduce the prevalence, morbidity, and healthcare costs associated with postoperative delirium remains to be determined.