Motivated by applications in unmanned aerial based ground penetrating radar for detecting buried landmines, we consider the problem of imaging small point like scatterers situated in a lossy medium below a random rough surface. Both the random rough surface and the absorption in the lossy medium significantly impede the target detection and imaging process. Using principal component analysis, we effectively remove the reflection from the air-soil interface. We then use a modification of the classical synthetic aperture radar imaging functional to identify and locate targets that allows for tunably high (subwavelength) resolution. We also propose a method for estimating the frequency dependent reflectivity of a dispersive target and show some preliminary results that may allow for classification of targets by their material properties, for example.