For many industrial, medical and space technologies, cryogenic fluids play irreplaceable roles. When any cryogenic system is initially started, it must go through a transient chill down period prior to normal operation. Chilldown is the process of introducing the cryogenic liquid into the system, and allowing the system components to cool down to several hundred degrees below the ambient temperature. The chilldown process is an important initial stage before a system begins functioning. The objective of this paper is to investigate the chilldown process associated with a flexible hose that was simulated by a channel with saw-teeth inner wall surface structure in the current study. We have investigated the fundamental physics of the two-phase flow and quenching heat transfer during cryogenic chilldown inside the simulated flexible hose through flow visualization, data measurement and analysis. The flow pattern developed inside the channel was recorded by a high speed camera for flow pattern investigation. The experimental results indicate that the chilldown process that is composed of unsteady vapor-liquid two-phase flow and phase-change heat transfer is modified by the inner wall surface wavy structure. Based on the measurement of the channel wall temperature, the teeth structure and the associated cavities generally reduce the heat transfer efficiency compared to the straight hose. Furthermore, based on the measured data, a complete series of correlations on the heat transfer coefficient for each heat transfer regime was developed and reported.