A prospective study was conducted to determine the relationship of serum nonesterified fatty acids (NEFA) and cholesterol concentrations and herd management practices to the occurrence of metritis, mastitis and retained placenta in Holstein cows in Michigan. Serum samples were collected once prepartum and once postpartum from 257 cows. Animals were under observation for disease occurrence from the date of calving until 3 months postpartum. Metabolic variables used were (1) prepartum only; (2) postpartum only; (3) the NEFA/cholesterol ratio for both pre- and postpartum samples. Management variables included maternity management, feed management, and factors such as season and parity. Multivariable logistic models with random-effect terms to account for the herd effect were used for data analysis. Results showed that: (1) metabolic events associated with energy insufficiency-increased fat mobilization and serum lipoprotein metabolism-were related to increased risk of metritis and retained placenta; (2) higher energy consumption during the last weeks of the dry period might reduce disease risk at parturition; (3) serum NEFA and cholesterol concentrations have potential as indicators of disease risk in dairy cows.