This research investigates spray phase transitions under subcritical and transcritical conditions relevant to high-pressure combustion systems. Using advanced optical diagnostic techniques, including shadowgraphy (SH), Mie scattering (MS), and infrared radiation (IR) measurements, the study focuses on cyclopentane sprays in a high-pressure, high-temperature chamber filled with gaseous nitrogen. Three cases are studied to understand spray behavior under varying injection conditions. SH and MS analyses reveal significant differences across the cases. As the chamber temperature increases, the liquid core length shortens, indicating enhanced vaporization. This is particularly evident in the MS images, where step-like transitions in the axial distribution highlight abrupt phase changes from liquid to gas in subcritical conditions. Such transitions are absent under supercritical conditions, suggesting a smoother phase transition process. IR measurements provide additional insights into the spray dynamics, especially under transcritical conditions. The IR images display complex downstream (at x/D > 125) signal patterns with bimodal distributions. The application of inverse Abel deconvolution highlights negative intensities near the spray axis downstream, indicative of regions near the pseudo-critical temperature. This phenomenon, characterized by blocked background radiation due to critical opalescence, offers indirect evidence of the pseudo-critical temperature and the associated phase transition dynamics. Dynamic Mode Decomposition (DMD) analysis identifies dominant frequencies around 4.5 kHz, corresponding to injection pressure fluctuations. This correlation suggests that injection pressure variations significantly influence spray fluctuations. Differences in mode shapes among the cases are also observed; lateral fluctuations near the injector nozzle exit are present in Cases 1 and 2 but not in Case 3. Axial fluctuations beyond a certain length are consistent in all cases. The lateral fluctuations are related to the chamber pressure and the potential large-scale vortex formation or cavitation in the nozzle. The combined use of SH, MS, and IR methodologies provides a comprehensive understanding of transcritical spray dynamics, emphasizing the effectiveness of combining multiple optical diagnostic techniques. These findings will improve numerical simulations and contribute to the development of more efficient high-pressure combustion systems. The research underscores the complexity of phase transitions in sprays and the critical role of precise diagnostics in the advancement of combustion technology.