The objective of this study was to evaluate the effect of calving-related disorders/clinical diseases (DIS) and cytological endometritis (CYTO) on the reproductive performance and culling of dairy cows. In a total of 119 multiparous Holstein cows, DIS were recorded and CYTO was diagnosed at 40 ± 2 d in milk. Onset of luteal activity was defined as the first postpartum measurement of milk progesterone >5 ng/mL. A dummy variable containing all four possible permutations between DIS and CYTO statuses was created. The pregnancy rates after first artificial insemination were 57.7, 42.9, 23.0 and 15.8% for the DIS−/CYTO−, DIS+/CYTO−, DIS−/CYTO+ and DIS+/CYTO+ groups, respectively. The hazard of pregnancy was affected by DIS−/CYTO+ and DIS+/CYTO+ health statuses (hazard ratio (HR) = 0.43 and 0.29, respectively), whereas DIS+/CYTO− and DIS−/CYTO− cows had a similar hazard to pregnancy. The hazard of onset of luteal activity was affected by DIS+/CYTO+ health status (HR = 0.45), but not by DIS+/CYTO− and DIS−/CYTO+ health statuses. Compared with DIS−/CYTO− cows, DIS−/CYTO+ and DIS+/CYTO+ cows had 4.24 and 5.57 times the odds of being culled, respectively. Culling was not affected by DIS+/CYTO− health status. In conclusion, CYTO+ status, irrespective of DIS status, decreased the pregnancy rate. When DIS+ and CYTO+ were combined, they had an additive negative effect. Our preliminary findings suggest that the far-reaching consequences of clinical diseases on fertility and culling can be mediated through the development of CYTO. Further investigations including a larger number of cows are required to confirm these results.