In the evolving educational landscape of the 21st century, technological engagement has become a central component in the development of innovative teaching and assessment strategies. This study investigated the relationship between technological engagement and creative classroom assessment among private secondary school students in Rivers State, Nigeria. A correlational research design was employed using a sample of 100 students selected from a population of 1,000 across registered private secondary schools in the state. Data were collected through a validated instrument titled the Technological Engagement and Creative Classroom Assessment Questionnaire (TECCAQ), which yielded a Cronbach Alpha reliability coefficient of 0.88. Results from the regression analysis indicated that Google Classroom usage accounted for 68% of the variance in creative assessment outcomes, while SmartBoard usage accounted for 32%. Both relationships were statistically significant (p < 0.001). These findings highlight the substantial role digital tools play in fostering creativity, collaboration, and performance-based assessment. The study recommends broader adoption of digital platforms in public schools and sustained teacher training to support technology-integrated assessment practices.