Milk production in Switzerland is mainly based on herbage feeding with little input of concentrates. The present study investigated the effects of a solely herbage-based diet with (C) and without concentrate (nC) supplementation on luteal activity, milk production and metabolic status in 23 multiparous Holstein dairy cows with early or delayed resumption of ovarian cyclicity post partum (pp). Cows were retrospectively assigned either to a group with early (until d 25 pp, EOV) or delayed resumption of ovarian activity (> d 30 pp, DOV), resulting in four subgroups depending on concentrate feeding: DOV-C, DOV-nC, EOV-C, EOV-nC. Milk progesterone (P4) concentration was measured every 3 d, and different metabolites were analyzed in weekly blood samples. Resumption of ovarian activity was detected between d 19 and 25 pp in EOV, and between d 30 and 60 pp in DOV. In DOV-C, resumption of cyclicity tended to start earlier (38.3 ± 1.7 d pp) compared to DOV-nC (45.2 ± 6.3 d pp; P = 0.10). Independent of grouping, the ovarian activity occurred later in cows with greater plasma β-hydroxybutyrate (BHB) concentrations (P < 0.05). Milk P4 concentration at the first rise > 1 ng/mL did not differ between groups (P > 0.05), but milk P4 peaks during the experiment were higher in EOV compared to DOV (P < 0.05). Cows of DOV-nC experienced the most negative energy balance during the first 3 weeks pp with concomitantly lowest plasma glucose and highest concentrations of non-esterified fatty acids and BHB. Insulin-like growth factor-1 concentrations were lower in cows without concentrate supplementation, but not related to EOV or DOV (P = 0.61). Overall, concentrate supplementation caused an earlier onset of luteal activity in cows in herbage-based feeding systems. Resumption of ovarian activity in cows with DOV was further delayed if energy and nutrient supply were limited.