Vitamin E is an essential nutrient for cows, but the effect of vitamin E supplementation is often controversially discussed in the published literature. The main goal of this meta-analysis was to evaluate the effects of vitamin E supplementation on its serum and colostrum enrichment, milk yield (MY), and somatic cell counts (SCC), as well as on various reproductive variables of transition cows, by considering a large set of variables that might influence the responses to vitamin E supplementation. After a broad search in journals and databases with keywords related to transition cows supplemented with vitamin E and appropriate filtering of the results, 36 papers including 53 trials were selected, and their data were extracted into a database. A meta-analysis was conducted on the extracted data. The analysis showed enrichment of serum vitamin E both at parturition (effect size: 2.423) and postpartum (effect size: 0.473), but no effects of vitamin E supplementation on IgG concentration in colostrum (effect size: −0.05) were found. There was a tendency for supplemented cows to produce more milk (effect size: 1.29) during the first month of lactation. Because of large heterogeneity, a meta-regression was performed but none of the presumed influencing factors was identified as a potential variable affecting MY. Milk SCC, as an indicator of udder health, was unaffected by vitamin E supplementation. Vitamin E supplementation tended to decrease the calving to first estrus period (CFP), whereby supplementing Se and taking parity into account in the analysis significantly lowered the CFP. Cows receiving additional vitamin E had, on average, 6.1% fewer cases of retained placenta, whereby Se supplementation and breed were key factors improving the effect of vitamin E to reduce retained placenta. In this regard, breeds other than Holstein responded better and these cows showed a lower incidence of retained placenta. The supplemented cows showed fewer days open (effect size: −0.31), and this improvement was affected linearly by increasing the dosage administered. Also, cows showed fewer services per conception with increasing dosage of vitamin E. In conclusion, this analysis showed that supplementing vitamin E did not affect SCC or colostrum quality but improved reproductive performance of transition cows, an effect consistent with increased levels of serum vitamin E and, for some variables, being modulated by Se supplementation.