The present study investigated the associations that student gambling and risk gambling share with a) students’ own experiences of their situation in school, b) school performance, and c) truancy. Data from the 2020 Stockholm School Survey were used, with information collected among 10,901 students in grades 9 (15–16 years) and 11 (17–18 years) from 145 schools in Stockholm Municipality. The studied school-related factors were school satisfaction, perceived teacher caring, perceived school order, school performance, and truancy. Binary logistic regression analyses were performed, with robust errors clustering at the school level. Students’ perceived teacher caring and perceived school order were inversely associated with both gambling and risk gambling, while truancy was positively associated with both gambling and risk gambling, even when mutually adjusting for all school-related factors simultaneously. School satisfaction was inversely associated with gambling, and school performance was inversely associated with risk gambling, when mutually adjusting for all school-related factors simultaneously. In sum, more positive experiences of the situation in school, higher school performance, and not playing truant were linked with a lower likelihood of gambling and risk gambling among students. The findings suggest that students’ situation in school can help to identify those at risk for gambling problems.