The enhancement of heat transfer continues to be a critical objective across various high-performance applications, including electronics cooling, automotive thermal systems, and renewable energy systems. Among emerging passive and active strategies, oscillating fin technology has attracted growing interest due to its potential to disrupt thermal boundary layers and augment convective heat transfer. In this review, a systematic analysis of 120 peer-reviewed studies indexed in Scopus, Web of Science, and Google Scholar was conducted, employing the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) methodology to ensure transparency and reproducibility. Search terms such as “oscillating fins,” “heat transfer enhancement,” “numerical simulations,” and “experimental techniques” were used to capture the breadth of relevant literature. Emphasis was placed on the interplay between oscillation parameters—namely frequency, amplitude, and mode of oscillation—and fin geometry, with particular focus on their influence on local and average heat transfer coefficients. Numerical methodologies, including Computational Fluid Dynamics (CFD) and Finite Element Thermal Analysis (FETA), were utilized extensively to characterize fluid motion and thermal gradients around oscillating structures. The reliability of these simulations was critically assessed in light of experimental validations, with instrumentation precision and laboratory conditions considered as key metrics of model fidelity. Challenges related to continuous fin movement, mechanical fatigue, and manufacturing constraints were also identified. To address these issues, recent developments in fatigue-resistant composite materials and advanced fabrication techniques—such as additive manufacturing—were reviewed. Furthermore, the incorporation of novel materials, including porous metals, nanofluids, and piezoelectric components, was explored for their synergistic effects on thermal performance and system durability. This review not only consolidates the current understanding of oscillating fin mechanisms but also highlights gaps in knowledge and opportunities for future research in the development of high-efficiency thermal management systems.