The article investigates the transitions of graduates of a middle-sized Italian university into the provincial labour market. University of Perugia administrative information and data from the job centres in the province are matched to reconstruct the timing of the university-to-work transitions of graduates since January 2004 to July 2009. Cox proportional hazard model with competing risk is used to determine the role of individual and studying characteristics in affecting the employment probabilities of graduates. Our main findings concern the relevance of degree specialization and accumulation of generic job experiences. Controlling for selection due to unobserved transitions of graduates finding a job outside the province of Perugia does not change our results significantly. Even though our results cannot be generalized to the national context, they constitute an innovative step of analysis to derive crucial considerations and policy implications concerning the transition of graduates into the local labour market.