Military personnel rely on caffeinated products such as coffee or energy drinks (ED) to maintain a maximal level of vigilance and performance under sleep-deprived and combat situations. While chronic caffeine intake is associated with decreased sleep duration and non-restful sleep in the general population, these relationships are relatively unclear in the military personnel. We conducted a focused review of the effects of caffeinated products on sleep and the functioning of military personnel. We used a pre-specified search algorithm and identified 28 peer-reviewed articles published between January 1967 and July 2019 involving military personnel. We classified the findings from these studies into three categories. These categories included descriptive studies of caffeine use, studies evaluating the association between caffeinated products and sleep or functioning measures, and clinical trials assessing the effects of caffeinated products on functioning in sleep-deprived conditions. Most of the studies showed that military personnel used at least one caffeine-containing product per day during active duty and coffee was their primary source of caffeine. Their mean caffeine consumption varied from 212 to 285 mg/day, depending on the type of personnel and their deployment status. Those who were younger than 30 years of age preferred ED use. Caffeine use in increasing amounts was associated with decreased sleep duration and increased psychiatric symptoms. The consumption of caffeinated products during sleep deprivation improved their cognitive and behavioral outcomes and physical performance. Caffeine and energy drink consumption may maintain some aspects of performance stemming from insufficient sleep in deployed personnel, but excessive use may have adverse consequences.