Catalytic transformations of levoglucosan (1-6-anhydro-β-D-glucopyranose) and furfural were carried out in a fixed-bed reactor at 573 K over mesoporous materials. Proton forms of MCM-41, MCM-48, SBA-15, and platinum form of MCM-48 catalysts were tested in the reaction, whereas H-Beta and quartz sand were used as reference materials. The yield of the transformation products was substantially influenced by the catalyst structures. Oxygenated species were the main liquid products, consisting mainly of aldehydes and furfural. The formation of furfural was the highest over MCM-41 catalyst followed by SBA-15, MCM-48, and H-Beta catalyst. All catalysts were to some extent deactivated due to coke formation. However, it was possible to successfully regenerate the spent catalysts without changing the structure.