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Many of the world’s agricultural frontiers are located in the tropics. Crop and cattle expansion in these regions has a strong environmental impact. This paper examines land use and land cover transformations in Brazil, where large swaths of natural vegetation are being removed to make way for agricultural production. In Brazil, the land use dynamics are of great interest regarding the country’s sustainable development and climate mitigation actions, leading to the formulation and implantation of public policies and supply chain interventions to reduce deforestation. This paper uses temporal trajectory analysis to discuss the patterns of agricultural practices change in the different biomes of Mato Grosso State, one of Brazil’s agricultural frontiers. Taking yearly land use and cover classified images from 2001 to 2017, we identified, quantified, and spatialized areas of stability, intensification, reduction, interchange, and expansion of single and double cropping. The LUC Calculus was used as a tool to extract information about trajectories and trajectories of change. Over two decades, the land use change trajectories uncover the interplay between forest removal, cattle raising, grain production, and secondary vegetation regrowth. We observed a direct relationship between the conversion of forest areas to pasture and of pasture to agriculture areas in the Amazon portion of the Mato Grosso State in different periods. Our results enable a better understanding of trends in agricultural practices.