The incorporation of novel technologies such as artificial intelligence, data mining, and advanced statistical methodologies have received wide responses from researchers. This study was designed to model the factors impacting the actual milk yield of Holstein–Friesian cows using the proportional odds ordered logit model (OLM). A total of 8300 lactation records were collected for cows calved between 2005 and 2019. The actual milk yield, the outcome variable, was categorized into three levels: low (< 4500 kg), medium (4500–7500 kg), and high (> 7500 kg). The studied predictor variables were age at first calving (AFC), lactation order (LO), days open (DO), lactation period (LP), peak milk yield (PMY), and dry period (DP). The proportionality assumption of odds using the logit link function was verified for the current datasets. The goodness-of-fit measures revealed the suitability of the ordered logit models to datasets structure. Results showed that cows with younger ages at first calving produce two times higher milk quantities. Also, longer days open were associated with higher milk yield. The highest amount of milk yield was denoted by higher lactation periods (> 250 days). The peak yield per kg was significantly related to the actual yield (P < 0.05). Moreover, shorter dry periods showed about 1.5 times higher milk yield. The greatest yield was observed in the 2nd and 4th parities, with an odds ratio (OR) equal to 1.75, on average. In conclusion, OLM can be used for analyzing dairy cows’ data, denoting fruitful information as compared to the other classical regression models. In addition, the current study showed the possibility and applicability of OLM in understanding and analyzing livestock datasets suited for planning effective breeding programs.