Introduction: This study explores the effectiveness of differentiated assessment as a strategy to support diverse learners in multi-level K–12 classrooms in Manitoba, Canada. Literature Review: Articles published from 2005 onward were sourced from ProQuest, ERIC, Google Scholar, ResearchGate, and Taylor & Francis databases. Methodology: A qualitative document review was employed by analyzing peer-reviewed articles. The review investigates how differentiated assessment practices, such as varied formats, flexible timing, assistive technologies, and constructive feedback, enable educators to identify students’ strengths, interests, and learning needs. Insights inform the adaptation of instructional plans to accommodate diverse learning styles and promote academic equity. Findings and conclusions reveal that while differentiated assessment fosters inclusivity and meaningful evaluation, implementation is hindered by challenges, including limited resources, insufficient teacher training, time constraints, and resistance to change. The findings contribute to ongoing discourse on equitable assessment practices and offer practical implications for enhancing student success in diverse educational settings. Recommendations: The study recommends targeted professional development, increased teacher autonomy, and collaborative efforts among educators and administrators to address these barriers.