Unhealthy behaviors initiated at a young age tend to remain in adulthood. Accumulation of unhealthy behaviors has cumulative negative effects on health status. The aim of this study was to examine patterns of co-occurrence of unhealthy behaviors (smoking, physical inactivity, high sugar intake, low fruit and vegetable intake, and infrequent tooth brushing) among younger and older Saudi male adolescents. A stratified cluster random sample of 1213 Saudi Arabian male school students living in Riyadh city answered the adapted WHO Health Behavior in School-Aged Children (HBSC) questionnaire on health-related behaviors. The co-occurrence patterns of unhealthy behaviors were assessed using an observed-to-expected ratio (O/E) method. The results showed that the pattern of three unhealthy behaviors (smoking + high sugar intake + physical inactivity) co-occurred with the highest O/E ratio of 3.16 among younger adolescents. In comparison, the pattern of (smoking + high sugar intake + low fruit/vegetables intake) was high among older adolescents with O/E: 1.67. The current study identifies patterns of unhealthy behaviors among younger and older Saudi male adolescents. Identification of these patterns is important for health promotion interventions.