Optical technologies are widely used for tissue sensing purposes. However, maneuvering conventional probe designs with flat-tipped fibers in narrow spaces can be challenging, for instance during pelvic colorectal cancer surgery. In this study, a compact side-firing fiber probe was developed for tissue discrimination during colorectal cancer surgery using diffuse reflectance spectroscopy. The optical behavior was compared to flat-tipped fibers using both Monte Carlo simulations and experimental phantom measurements. The tissue classification performance was examined using freshly excised colorectal cancer specimens. Using the developed probe and classification algorithm, an accuracy of 0.92 was achieved for discriminating tumor tissue from healthy tissue.