Objectives: This study aimed to elucidate the effects of two naps taken at night on morning waking state and performance. Methods: The participants were 12 women. The experiment was performed in a laboratory over 2 days (16:00-09:00). In this crossover comparative study, three experimental nap conditions were used (naps from 22:30 to 00:00 and from 02:30 to 03:00 (22:30-NAP), 00:30 to 02:00 and 04:30 to 05:00 (00:30-NAP), and no naps (NO-NAP), respectively). Measurement items were a Visual Analog Scale for sleepiness and fatigue, the Psychomotor Vigilance Test (PVT), and single-digit addition calculations (10 min) every hour for 18 h from 16:00 to 09:00, excluding nap times. Results: Sleep inertia and sleepiness were noted directly after napping. Less sleepiness and fatigue were noted in the nap groups between 06:00 and 09:00 in the morning than in the NO-NAP condition and PVT response times were faster. Since participants in the nap groups were able to conduct more single-digit addition calculations, the performance of these groups appeared to be superior to that of the NO-NAP condition. Furthermore, the performance of calculations was significantly better in the 00:30-NAP than in the 22:30-NAP. Conclusions: Taking two naps during a simulated night shift helps improve sleepiness and fatigue and maintain performance. Taking a nap in the early morning appears to be promising for improving the waking state.