The systematic review brings together an empirical and theoretical literature on productive failure and desirable difficulties as pedagogical strategies that improve long-term learning retention and transfer in learning mathematics. The review examined 50 of the most relevant studies of a total of 334 candidate papers (collected in the form of references) in 33 different countries such as Singapore and Korea and other educational systems representing the objective of a systematic selection of literature that follows query expansion and citation chaining methodology. The thematic coding and frequency analysis adopted as an analytical framework were used to measure research emphasis in cognitive, pedagogical, and motivational levels in an analytical way. A statistical synthesis indicated that a total of thirty studies reported significant effects of cognitive activation with the use of productive failure interventions, whereas thirty-five studies reported a higher level of conceptual understanding and transfer performance in comparison with the use of direct instruction methods. Twelve studies showed sustained procedural fluency with productive failure, which puts assumptions of trade-offs of conceptual depth and proficiency into challenges. The implementation research provided collaboration problem solving and teacher-led consolidation as the most common twenty-five studies, and strategic questioning and sufficient struggle time were considered as key success factors in fifteen separate studies. As the result of the theoretical alignment analysis, forty studies were found to accommodate constructivist frameworks, twenty studies accommodated cognitive load perspectives, and fifteen studies were found to focus on motivation theories such as growth mindset and resilience. The use of technologies was still minimal, and the number of studies that revealed successful use of digital tools was fifteen, and ten studies discussed the possibility of using technology as the cognitive amplifier, which shows significant gaps in further research in technological integration. Cross-study synthesis was conducted with the use of comparative analysis of the approaches to activities of studies and their participants, as well as factors of the surroundings, to uncover patterns of effectiveness and issues of implementation