Competitive Tendering is perhaps the preferred approach for procuring Public Transport (PT) passenger services in the EU, according to its legislation. Cyprus has initiated a few years ago the second PT reform cycle which will be concluded with the awarding of six new concession contracts for passenger services by bus. This paper presents and discusses the two PT reforms in Cyprus. The aim of the second reform is to significantly increase the PT share by improving service availability and quality through the transition from a monopolistic to a more competitive PT market. According to the roadmap prepared by the Cypriot authorities, specific contracting arrangements have been set to attract both local and international PT operators to the competitive tendering process. These arrangements mostly pertain to the eligibility and selection criteria of the tendering process, the opportunity to lease PT buses from local companies and the contract type and duration. The paper sets five main questions addressing critical issues of the reform effort and provides responses through the in-depth analysis of the selected tender and contractual arrangements. Useful findings and conclusions may be drawn, especially regarding the effect of small size market and the lack of necessary PT infrastructure.