A total of 28,637 lactation records from 5,793 Holstein cows milked in a commercial herd (Granja San José, Huesca, Spain) between 2000 and early 2016 were used to assess the potential impact of dry period length (DPL) and level of milk production at dry-off (MPD) on milking performance during the first 100 DIM of the subsequent lactation. Cows were milked in a parlor equipped with electronic meters. All data were recorded and saved into a database on a daily basis. The database stored information about parity, fresh date, daily milk production, and date of dry-off. Milk production of each cow and lactation during the last 3 d preceding dry-off was averaged. Also, milk production during the first 100 DIM for each lactation was summed (cumulative daily milk) within cow. Both DPL and MPD were categorized following the quartiles of their distributions (1: ≥68 d, 2: between 64 and 68 d, 3: between 60 and 64 d, and 4: ≤60 d for DPL; and 1: ≥27.8 kg/d, 2: from 23.5 to 27.8 kg/d, 3: from 18.9 to 23.5 kg/d, and 4: ≤18.9 kg/d for MPD). A mixed-effects model was used to evaluate the fixed effects of lactation number, DPL, MPD, and their interactions, and the random effect of year. Cows with a DPL ≤60 d produced (4,608 ± 59 kg) less (P < 0.05) than cows with DPL >60 d (4,734 ± 61.9 kg), regardless of lactation number. Milk production before dry-off was positively correlated (P < 0.05) with milk production in the subsequent lactation, and this effect was more (P < 0.05) important in cows with an MPD <27.8 kg/d and a DPL ≤60 d (4,514 ± 78 kg) than in cows with an MPD ≥27.8 kg/d and a DPL ≤60 d (4,887 ± 81 kg), whereas the impact of production before dry-off was lower when cows had a DLP ≥68 d, with cows with an MPD ≥23.5 kg/d producing more milk (4,942 ± 87 kg) than those with an MPD <23.5 kg/d (4,605 ± 97 kg). Furthermore, a triple interaction was found between parity, DPL, and MPD, with milk production from cows with >5 lactations being barely affected by MPD and DPL. It is concluded that shortening DPL below 60 d compromises milk yield in the following lactation and this effect is exacerbated when milk production at dry-off is low, especially between lactations 2 and 5 (both included).