This study aimed to assess the relationship between the length of the dry period (DL) and the risks of dystocia and stillbirths in Holstein cows. A total of 1072 healthy cows in lactations 1 and ≥2 were categorized based on the DL (mean: 58.07 ± 0.33 days) into three groups: short DL (<40 days; 13.0% of cows), medium DL (40-70 days; 60.1%), and long DL (>70 days; 26.9%). Dystocia occurred in 12.4% of cows, while stillbirths accounted for 4.1% of calves. The medium DL group had the highest number of unassisted calvings. The dystocia rates were 11.4% for cows with gestation (GA) ≤ 274 days; 6.0% for cows with GA = 275-282 days; and 19.9% for cows with GA ≥ 283 days (p < 0.001). In season 1 (November-April), dystocia occurred in 15.0% of cases compared to 8.8% in season 2 (May-October) (p < 0.001). The stillbirth rates ranged from 3.6% to 4.0% for cows with medium and long DLs; while those with a short DL had 5.8% (p < 0.05). The stillbirth rates were 5.2% for cows with GA ≤ 274 days; 3.2% for cows with GA = 275-282 days; and 5.1% for cows with GA ≥ 283 days (p < 0.001). Season 1 had a stillbirth rate of 4.8%, while season 2 had a stillbirth rate of 3.3% (p < 0.001). This research provides insights that could assist the dairy industry in making informed decisions to reduce the incidence rates of dystocia and stillbirths in cows.