This paper presents an evaluation of two different Vehicle to Infrastructure (V2I) applications, namely Red Light Violation Warning (RLVW) and Green Light Optimized Speed Advisory (GLOSA). The evaluation method is to first develop and use Hardware-in-the-Loop (HIL) simulator testing, followed by extension of the HIL testing to road testing using an experimental connected vehicle. The HIL simulator used in the testing is a state-of-the-art simulator that consists of the same hardware like the road side unit and traffic cabinet as is used in real intersections and allows testing of numerous different traffic and intersection geometry and timing scenarios realistically. First, the RLVW V2I algorithm is tested in the HIL simulator and then implemented in an On-Board-Unit (OBU) in our experimental vehicle and tested at real world intersections. This same approach of HIL testing followed by testing in real intersections using our experimental vehicle is later extended to the GLOSA application. The GLOSA application that is tested in this paper has both an optimal speed advisory for passing at the green light and also includes a red light violation warning system. The paper presents the HIL and experimental vehicle evaluation systems, information about RLVW and GLOSA and HIL simulation and road testing results and their interpretations.