A system and a method for generating individualized academic worksheets are provided. The method includes accessing a database of problems and student data relating to at least one student, including evaluation data associated with practice worksheets that were previously administered to the students. The method further includes selecting problems from the database using the evaluation data for each student and generating an individualized practice worksheet file including the selected problems. Each practice worksheet file includes instructions for printing a presentation of each problem and at least one evaluation area. The method further includes updating the evaluation data, wherein after a printed copy of a practice worksheet file is administered to the student, the evaluation areas of the printed copy are marked with evaluation marks by a human evaluator in accordance with the human evaluator's evaluation, and the updated evaluation data is based on the evaluation marks.