Over the centuries, a multitude of problems has been raised in the field of stochastic processes and the combinatorics used within it, and these have been solved in highly ingenious ways. This book presents a selection of the most interesting problems in their historical sequence. Tasks and solutions are introduced in both their historical context and modern form. It is always surprising to see the methods and computational skills that were employed in earlier times to tackle these problems. The work offers inspiration for all interested parties, from mathematically educated laypeople to professional mathematicians. Many of the problems listed have had a significant impact on the development of problem culture in stochastic processes. To this day, traces of these can be found in the exercises of school and university textbooks. Content: From the beginnings to the end of the Middle Ages, the beginning of the modern era.