The objective of the present study was to evaluate the effects of postpartum oral calcium supplementation on milk yield, energy-corrected milk yield, milk fat concentration, milk protein concentration, and somatic cell count linear score across the first 3 monthly tests postpartum, peak milk yield, risk of pregnancy at first service, and hazard of pregnancy by 150 d in milk on 1,129 multiparous Jersey and Jersey × Holstein crossbreed cows from 2 commercial dairies. After calving, cows were systematically assigned to control (no oral calcium supplementation; n = 567) or oral calcium supplementation at 0 and 1 d in milk (oral Ca; 50 to 60 g of calcium as boluses; n = 562). Monthly test milk yield, composition, and somatic cell count information was obtained from the Dairy Herd Improvement Association. Herd records were used for reproductive data. Statistical analysis was conducted using generalized multiple linear, Poisson, and Cox's hazard regressions. Treatment effects were evaluated considering cow-level information available at parturition (parity, breed, previous lactation milk yield, previous lactation length, dry period length, gestation length, body condition, and locomotion score at calving, calving ease, and calf sex). In addition, for a subset of cows serum calcium concentration before treatment administration was evaluated (n = 756). Overall, oral calcium supplementation did not affect the evaluated productive and reproductive variables. However, effects conditional to previous lactation length and calving locomotion score were observed. Milk yield and energy-corrected milk yield across the first 3 monthly tests were 1.8 kg/d higher for supplemented cows with a previous lactation length within the fourth quartile, compared with control cows on the same quartile. Energy-corrected milk yield tended to be 1.1 kg/d lower for supplemented cows with a previous lactation length within the first quartile, compared with control counterparts. Peak milk yield tended to be 1.6 kg higher for supplemented cows with a calving locomotion score ≥2, compared with control cows with the same locomotion score. Treatment effects were not conditional to serum calcium concentration before treatment administration. Our results suggest that postpartum oral calcium supplementation effects are conditional to cow-level factors such as previous lactation length and calving locomotion score in multiparous Jersey and Jersey × Holstein crossbreed cows.