The primary objective was to investigate the association between delayed milk ejection (DME) and the average milk flow rate, milking unit-on time, and duration in a low milk flow rate in Holstein dairy cows in a large dairy herd with suboptimal premilking teat stimulation. Our second objective was to study the association between peak lactation milk yield and the occurrence of DME. This longitudinal field study was conducted at a 4300-cow dairy farm with a thrice-daily milking schedule over a 1-week period. We analyzed data from 61,677 cow milking observations from 2937 cows. Delayed milk ejection was defined as present if the 30–60 s milk flow rate was ≤3.1 kg/min. The mean average milk flow rate (MAMF, kg/min), mean milking unit-on time (MMUT, s), and mean duration of a low milk flow rate (MLMF, s) were calculated as the mean values from the 21 milking observations. General linear multivariable models revealed associations of DME with MAMF, MMUT, and MLMF. A multivariable ordinal logistic regression model revealed an association between peak lactation milk yield and DME. Cows with lower peak lactation milk yield had greater odds of exhibiting a higher frequency level of DME. The observed associations between DME and milking performance indices suggest that DME can negatively affect milking and parlor efficiency. Peak lactation milk yield may serve as a proxy to estimate cows’ risk of recurrent DME. Future research is warranted to test if alleviating DME through, for example, a modified milking routine influences the milking performance indices described herein.