Sleepiness is an important consideration for workplace safety, especially in relation to shift work. There is limited understanding of how practical applications of countermeasures are used to manage sleepiness in a professional setting. One under-researched group is city bus drivers. This qualitative study investigated the use of individual sleepiness countermeasures within a sample of city bus drivers. Nine semi-structured focus groups were convened to explore the broader experience and management of sleepiness (n = 62, largest proportion aged 45–54 y, mean bus driving experience 13.3 y). The conversations of the focus groups were audio-recorded (total: 682 min) and transcribed anonymously verbatim. Discussions specifically relating to personal countermeasure use were isolated from the original transcripts, creating nine new transcripts for a targeted analysis on the topic of individual countermeasure use. Thematic analysis identified two main themes: (1) strategies used to counteract sleepiness and (2) barriers to individual countermeasure use, each with several subthemes. A variety of countermeasures were used, including strategies with limited potential for counteracting sleepiness, such as opening a window, drinking water, talking, stretching, and consuming forms of sugar. Workplace restrictions, such as access to facilities, limitations of food/drink consumption, and tight schedules, were the strongest influences on countermeasure choice. It is important that bus drivers have access to, and are aware of the effectiveness of, countermeasures to manage sleepiness during shift work. It is vital that the actions of drivers and shift workers are better understood in the planning of organizational countermeasures.