Our objectives were to investigate the association of teat shape with (1) bimodality, (2) incremental milk flow rates (average flow rates during the first 15 s, 15-30 s, 30-60 s, and 60-120 s of milking), and (3) peak milk flow rate in Holstein dairy cows milked 3 times/d. In this prospective cohort study, we analyzed 220,928 milking observations that were collected from 2,520 cows from a single dairy herd over a period of 31 d. Teat shape was visually assessed and classified into 1 of 4 categories as follows: (1) triangular barrel and pointed teat end (TP), (2) square barrel and round teat end (SR), (3) square barrel, round teat end, and flat in the area of the teat orifice (SRF), and (4) square barrel and flat teat end (SF). Individual cow-level milk flow rates were obtained using electronic on-farm milk meters. We considered bimodality to be present if any of the incremental milk flow rates (flow rates during 15-30 s, 30-60 s, or 60-120 s) were lower than any of the previous rates (flow rates during the first 15 s, 15-30 s, or 30-60 s). The frequency distribution of cows with different teat shapes was as follows: TP, 96 (3.8%); SR, 1,751 (69.5%); SRF, 617 (24.5%); and SF, 56 (2.2%). A generalized linear mixed model revealed differences in the odds of bimodality among cows with different teat shapes. Compared with cows in category SR, the odds (95% CI) of bimodality of cows in other categories were as follows: TP, 0.68 (0.48-0.97); SF, 1.96 (1.21-3.19); and SRF, 1.46 (1.23-1.72). General linear mixed models indicated an association between teat shape and all incremental milk flow rates, with higher milk flow rates being present for cows with teat shapes in the SRF and SF categories. The general linear mixed model for the dependent variable peak milk flow rate indicated an association between teat shape and peak milk flow rate. Least squares means and 95% CI were 5.1 (4.9-5.3) kg/min for TP, 5.8 (5.5-6.1) kg/min for SF, 5.6 (5.5-5.7) for SRF, and 5.3 (5.3-5.4) for SR, respectively. We conclude that in this study cohort, bimodality is more likely to occur in cows with flat teat ends compared with those with a round teat ends. We attribute this relationship to the difference in milking speed across cows with different teat shapes. Teat shape may serve as a useful phenotype to identify cows that are more likely to exhibit bimodality. Because our study population was unique, future studies considering different circumstances such as breed, milking system, and milking routine are needed before results can be extrapolated.