Doenjang (fermented soybean paste) and ganjang (soy sauce) are traditional fermented foods that are widely consumed in Korea. The oligosaccharides found in soybean and its fermented foods have great potential to improve the quality of foods; however, their structural details have not been well studied. In this study, we used advanced mass spectrometry and gas chromatography to analyze oligosaccharides and their monomeric composition in two fermented soybean products. In both foods, oligosaccharides with a degree of polymerization ranging from 3 to 7 were found. Their constituent monosaccharides were characterized; galactose, xylose, arabinose, and rhamnose were the predominant constituents of the oligosaccharides, and fucose, fructose, mannose, glucose, and N-acetylglucosamine were also found. The great structural diversity of the oligosaccharides found suggests that soybean carbohydrates are hydrolyzed and/or transformed during fermentation and may yield novel oligosaccharides.