A cooling system using oscillating heat pipe (OHP) has been developed for a balloon-borne astrophysics project GAPS (General Anti-Particle Spectrometer). Taking advantages of OHP, such as high conductivity, low-power, and suitability for spread heat source, OHP is planned to be used to cool the GAPS core detectors. OHP is a novel technique and it has never been utilized in practical use neither for a spacecraft nor for a balloon-craft, regardless of its many advantages. In these several years, we have investigated OHP's suitability for GAPS step by step. At first, we have succeeded in developing a scaleddown OHP model with a three-dimensional routing, which can operate in a wide temperature range around between 230 K and 300 K. We also succeeded in the first OHP flight demonstration with a prototype GAPS balloon experiment. Subsequently, we developed actual-sized OHP models with various routings. Numerical simulation models have been developed in parallel to further optimize the OHP design by understanding the OHP performance both macroscopically and microscopically. The design of the OHP check valve has been improved as well. This paper discusses the latest status of the GAPS-OHP development.