MicroRNAs (miRNAs) in cancer development have attracted much attention in recent years. miR‐29 is known to critically affect cancer progression by functioning as a tumor suppressor. However, it may also act as an oncogene under certain situations. The prognostic value of the miR‐29 family in cancer progression is still under debate and reported results are inconsistent. Therefore, we reported here a meta‐analysis and systematic review to analyze the prognostic role of the miR‐29 family in cancer. We screened 20 published studies and calculated pooled hazard ratios (HRs) and corresponding 95% confidence intervals (CIs) for overall survival (OS) or disease‐free survival/recurrence‐free survival (DFS/RFS). Our results showed that a low or absent expression of miR‐29 family was significantly associated with poor OS (HR, 1.57; 95%CI, 1.18‐2.08), and inferior to 5‐year DFS/RFS (HR, 1.89; 95%CI, 1.47‐2.44). Analysis of individual miR‐29 subtypes indicated that the low expression of miR‐29a/b/c subtypes correlated with poor 5‐year OS (miR‐29a: HR, 1.99; 95%CI, 1.41‐2.80; miR‐29b: HR, 1.60; 95%CI, 1.18‐2.17; miR‐29c: HR, 1.69; 95%CI, 1.00‐2.86), as well as poor 5‐year DFS/RFS (miR‐29b: HR, 1.70; 95%CI, 1.27‐2.27). Ethnicity analysis demonstrated Asian patients with low expression of miR‐29 were significantly correlated with poor OS (HR, 1.61; 95%CI, 1.16‐2.23) and 5‐year DFS/RFS (HR, 2.03; 95%CI, 1.50‐2.74). Taken together, our analysis indicates that the low expression of miR‐29 is associated with aggressiveness and poor prognosis of malignant neoplasms. More importantly, miR‐29 might serve as a key biomarker for predicting the recurrence and progression of human cancers.