This work provides one of the most comprehensive datasets to date on the chemical evolution of poplar wood polysaccharides and their degradation products during dilute acid pretreatment. Based on the literature, an unprecedented set of 38 conditions was generated using a design of experiment approach within the following parameter ranges: 2–60 min, 120–190 °C, 0–4%wt H2SO4. Solid wood residues and pretreatment liquid, recovered separately, were analyzed for no less than 12 compounds: sugars, inhibitors, and lignin. Particular attention was paid to the sampling and method description so that the dataset, fully available, can be easily shared and reused. This unique dataset was explored using models to follow the evolution of each chemical species. A more original and in-depth analysis was carried out by combining the models using desirability functions, which enabled us to propose trade-offs between the evolution of the different compounds according to the targeted production objectives.