In this work, the performance of eight prominent empirical path loss models and a localized model, in predicting path losses in build up areas is investigated. Multi electromagnetic field strength measurements were conducted, using a dedicated spectrum analyzer, along five predefined routes in Osun State, Nigeria. The measured data were compared with the model predictions. Path profile and terrain undulations effects have been observed on the received signal. For all the routes and trans models over predicted the path losses, while Ericsson model under predicted the losses. However, Hata, Davidson, Cost 231 and ILORIN models generally show promising results with varying performance. The average mean error values of 55 dB, -28.16 dB, -8.93 dB, -30.59 dB, -22.95 dB and OSOGBO transmitter for Okumra, Hata, SUI, Cost 231, CCIR, Davidson, Ericsson, EEC and ILORIN models. In terms of RMSE, the av 9.18 dB were obtained for ILORIN, Hata and Davidson models found to be similar for other transmitters i.e. OSBC, NDTV and NTA Ile Ife with varying performances among the four contending performance for the two main contending models i.e. ILORIN and Hata models. Inconsistency in terms of the performance for each model were observed, however the localized model i.e. ILORIN was found to provide optimum path loss prediction with considerable accuracy, over the other models. With the aforementioned, we believe the results and observations presented would provide guide to radio system engineers in making informed choices on the applicability and predictability of such models in the terrain of Osun State and other similar build Nigeria.