Background: The objectives of this systematic review and meta-analysis were to quantify the effectiveness of endurance training (ET) on aerobic performance (i.e., peak oxygen uptake (VO2peak)) in healthy and unhealthy middle and very old adults aged 70 years and older, and to provide dose–response relationships of training prescription variables (in terms of frequency, and volume). Methods: Several scholarly databases (i.e., PubMed/MEDLINE, SpringerLink, ScienceDirect Journals, and Taylor & Francis Online—Journals) were searched, identifying randomized controlled studies that investigated the effectiveness of ET on VO2peak in older adults. Standardized mean differences (SMD) were calculated. Results: In terms of changes differences between experimental and control group, ET produced significant large effects on VO2peak performance (SMD = 2.64 (95%CI 0.97–4.31)). The moderator analysis revealed that “health status” variable moderated ET effect onVO2peak performance. More specifically, ET produced larger SMD magnitudes on VO2peak performance in healthy compared with unhealthy individuals. With regard to the dose–response relationships, findings from the meta-regression showed that none of the included training prescription variables predicted ET effects on VO2peak performance. Conclusions: ET is an effective mean for improving aerobic performance in healthy older adults when compared with their unhealthy counterparts.