The application of in-situ Raman spectroscopy in microcapsule-based cementitious materials provides an accurately approach to evaluate the self-repairing mechanism of the microcapsules. In this paper, the microcapsules with enhanced Raman spectroscopy sensitivity was prepared and the in-situ Raman spectroscopy was applied to tracing the repairing process in cementitious matrix. Based upon the characterisation of the traditional UF/Epoxy microcapsule by Raman spectroscopy, the spectra of the microcapsule shell and core in cementitious matrix were identified and established. Furthermore, to improve the detection precision and efficiency, a newly designed microcapsule was developed in which the anatase was introduced in the microcapsule to amplify the signal by around 90 times. Finally, the healing behaviour of this newly designed microcapsule was investigated by Raman mapping. The results clearly showed that Raman spectroscopy successfully detected the breakage of microcapsule due to the occurrence of cracking, which provides a promising approach to detecting the repairing behaviour of self-healing microcapsules in cementitious materials.