We have developed a clinical probe capable of acquiring simultaneous short wavelength infrared (SWIR) cross-polarized reflectance and occlusal transillumination images of lesions on tooth proximal and occlusal surfaces. We hypothesize that the dual SWIR reflectance and transillumination probe will improve the diagnostic accuracy of the device by reducing false positives since it is unlikely that confounding structural features or specular reflection are going to be present in both reflectance and transillumination images. In addition, the dual probe will provide complementary diagnostic information about lesion severity to help discriminate early superficial lesions on tooth surfaces from deeply penetrating lesions. The dual probe was 3D printed and equipped with a compact InGaAs camera and broadband superluminescent diode light sources that emit broadband light at 1300 nm for occlusal transillumination and 1600 nm light for cross-polarization reflectance measurements. The first clinical images acquired using this novel probe are presented.