Cavitary corpora lutea are commonly observed during the estrous cycle in bovines. Since the quality of the corpus luteum (CL) is extremely important during embryo transfer when embryos are implanted into the recipient, the ultrasonographic examination of the CL is becoming more and more important in terms of the outcome of the procedure. In the present study, a total of 2477 ultrasonographic transrectal diagnoses were performed, and data were collected between the years of 2018 and 2020 in a large-scale Holstein Friesian dairy farm in Hungary. In 91.1% (n = 2257) and in 8.9% (n = 220) of the cases, compact CLs and cavitary CLs, respectively, were diagnosed at pregnancy diagnosis. The presence of a cavitary CL on the ovary at pregnancy diagnosis increased the odds of remaining open after pregnancy by 21 times compared to the presence of a compact CL (OR = 21.0, p < 0.001) in the cows. The presence of cavitary CL was not influenced either by month or season. Ovarian cysts were detected in 196 cases (8.0%) in the examined animals. The presence of a cavitary CL decreased by 9 times when an ovarian cyst was also diagnosed (OR = 9.0, 1.6% vs. 9.5%, p < 0.001). The presence of an ovarian cyst decreased the odds of established pregnancy by 81 times (OR = 81.1, p < 0.001). Based on our results, the presence of a cavitary CL between days 31 and 42 after artificial insemination is associated with a smaller chance of conception in Holstein Friesian cows. The presence of an ovarian cyst decreases the occurrence of cavitary CL and the chance of conception.