This chapter presents a critical analysis of the use of matchstick or toothpick puzzles in brain training and different areas of human learning in search of creativity. Fostering brain health is important in personal life, while fostering creativity is necessary for successful work in many professions. Special attention is given to the use of matchstick or toothpick puzzles in mathematics education. Through documental research, the presence and characteristics puzzles were analyzed in many mathematics textbooks, mainly in teacher’s editions. The results of the research, presented in the chapter, show that the use of matchstick or toothpick puzzles is far from adequate. Namely, the number of puzzles used is insufficient and they are prone for didactic improvement. The main failure is the presence of only one solution for multiple-solution puzzles (cognitive bias “one puzzle—one solution”).