In this study, we monitored the thermal formation of early ribose-glycine Maillard reaction products over time by ion cyclotron resonance mass spectrometry. Here, we considered sugar decomposition (caramelization) apart from compounds that could only be produced in the presence of the amino acid. More than 300 intermediates as a result of the two initial reactants were found after ten hours (100 °C) to participate in the interplay of the Maillard reaction cascade. Despite the large numerical variety the majority of intermediates follow simple and repetitive reaction patterns. Dehydration, carbonyl cleavage, and redox reactions turned out to have a large impact on the diversity the Maillard reaction causes. Although the Amadori breakdown is considered as the main Maillard reaction pathway, other reactive intermediates, often of higher molecular weight than the Amadori rearrangement product, contribute to a large extent to the multitude of intermediates we observed.