The phenolic content of olive oil has a role in cardiovascular protection. Some clinical trial studies demonstrated that phenolic compounds of olive oil have antioxidant activity which can protect macronutrients from oxidative damages. The aim of this study was to summarize the results of clinical trials which assessed the effects of high‐ versus low‐phenol olive oil on oxidative stress biomarkers levels. We searched Scopus, PubMed, Web of Science, Google Scholar, ProQuest, and Embase up to July 2021. Eight clinical trials which evaluated the effect of the phenolic content of olive oil on oxidized‐LDL (ox‐LDL), malondialdehyde (MDA), or ferric‐reducing ability of plasma (FRAP) were included the meta analysis. A significant decrease was observed in ox‐LDL level (WMD: −0.29 U/L; 95% CI: −0.51, −0.07) and MDA (WMD: −1.82 μmoL/L; 95% CI: −3.13, −0.50). However, after subgroup analysis for MDA, the result was not significant for not serious limitation (SMD: −0.05, 95% CI: −0.35 to 0.24), but significant for serious limitation (SMD: −3.64, 95% CI: −4.29 to −2.99). Also, no significant change was found in FRAP (WMD: 0.0 mmoL/L; 95% CI: −0.03, 0.04) level. Dose–response analysis indicated a significant linear relationship between the phenolic content of olive oil and ox‐LDL. The present study showed some beneficial effects of high‐phenol compared with low‐phenol olive oil on ox‐LDL and MDA levels. According to the meta‐regression analysis along with the increasing phenolic content of olive oil, a reduction in oxidative stress biomarkers was observed.