Background: Night shift work often implies shorter sleep duration and this can lead to sleepiness, which has been associated with an increased risk of accidents and injuries. The aim is to study how the number of consecutive night shifts affects self-reported sleepiness. Participants and methods: The study was a quasi-experimental, within-subject crossover study with 73 police officers. Three work schedules of two, four, and seven consecutive night shifts followed by the same number of recovery days, i.e., days worked or days off, was performed by all participants. Sleepiness was self-reported using the Karolinska sleepiness scale (KSS) every fourth hour on the last night shift and the last recovery day in each sequence. Results: We observed differences in the level of sleepiness between recovery days and night shift days but no differences in the pattern of sleepiness levels on night shift days in the different work schedules. The highest levels of KSS were observed before bedtime (at 07:00 after a night shift and 23:00 on a recovery day). Conclusion: The number of consecutive night shifts did not affect the self-reported levels of self-reported sleepiness among Danish police officers.