Sleep deprivation is a prevalent and rising health concern, one with known effects on blood glucose (BG) levels, mood, and calorie consumption. However, the mechanisms by which sleep deprivation affects calorie consumption (e.g., measured via self-reported types of craved food) are unclear, and may be highly idiographic (i.e., individual-specific). Single-case or “n-of-1” randomized trials (N1RT) are useful in exploring such effects by exposing each subject to both sleep deprivation and baseline conditions, thereby characterizing effects specific to that individual. We had two objectives: (1) To test and generate individual-specific N1RT hypotheses of the effects of sleep deprivation on next-day BG level, mood, and food cravings in two non-diabetic individuals; (2) To refine and guide a future n-of-1 study design for testing and generating such idiographic hypotheses for personalized management of sleep behavior in particular, and for chronic health conditions more broadly. We initially did not find evidence for idiographic effects of sleep deprivation, but better-refined post hoc findings indicate that sleep deprivation may have increased BG fluctuations, cravings, and negative emotions. We also introduce an application of mixed-effects models and pancit plots to assess idiographic effects over time.