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The ability of assembling inorganic, organic, and even bioactive components in a single material unfolds an exciting direction in the development of novel multifunctional hybrid materials. Recently, we have observed that the hydrophilic/hydrophobic character of the organic polymeric moieties determines the swelling/diffusion control of the drug release. In this work, the antitumor cisplatin (CisPt) molecules incorporated into the ureasil-PEO (poly(ethylene oxide)) hybrid material was used as a probe for the in situ and simultaneous UV-vis and Raman spectroscopies monitoring of the kinetics of both the water uptake as well as the CisPt release by the hybrid matrix. Drug molecules were incorporated during the hydrolysis and polycondensation steps. The monolithic xerogel were analyzed by X-ray absorption spectroscopy and differential scanning calorimetry, while the drug release properties were monitored by Raman as well as UV-vis spectroscopies. The results show that the molecular structure of the CisPt is preserved in the one pot sol-gel route used in synthesizing the CisPt-loaded PEO1900 hybrid. The in situ monitoring of water uptake clearly points out the key contribution of the osmotic flow on the stepped profile of the CisPt delivered from the PEO1900 hybrid matrix.