Purpose: The purpose of the study was to examine the trends between 2002 and 2018 in school pressure and school satisfaction among 15-year-old students, across countries and by gender, in the WHO European region and North America, and explore whether there are variations between countries and by gender in the co-occurrence of school pressure and school satisfaction.

Methods: Data from the 32 countries that participated in the Health Behaviour in School-aged Children study (HBSC) study between 2002 and 2018 were used. Statistical analyses included t-tests, binary logistic regression analyses, and chi-square tests, as required by each of the study aims.

Results: School satisfaction tended to increase over the period 2002–2018 among boys, whereas school pressure increased among girls. Also, gender differences tended to dissipate in school satisfaction and generally increase in school pressure. The co-occurrence of school satisfaction and school pressure in 2017/2018 shows that the majority of students are found in the “not pressured–not highly satisfied” and “pressured–not highly satisfied” groups. There were more boys in the former group and more girls in the latter group.

Conclusion: Few students in the 32 countries belonged to the “not pressured–highly satisfied” group, which from a public health perspective may be seen as the most desirable group. The increases in school pressure in girls from 2002 to 2018 and their overrepresentation in the pressured groups require further attention.