Needle-free connectors having a housing with an cavity and center-post, and valves having a head and a skirt are disclosed where the valve is positioned within the cavity of the housing with the center-post extending into a passage through the valve, and the skirt extending away from the head of the valve to the housing to fluidly separate the cavity into a first portion and a second portion, and where an outer end of the skirt is spaced apart from an end of the cavity to permit the valve to move between a closed configuration and an open configuration such that, in the open configuration, the skirt extends along the head and in a direction toward a first housing port, and as the valve moves from the open configuration toward the closed configuration, a volume of the first portion of the cavity decreases to expel any fluid accumulated therein.