The article is devoted to the Arab medical written monument of the Middle Ages — “Hundred Books on the Skills of Medicine” by the physician and polymath Abu Sahl Isa b. Yahya al-Masihi (approx. 970–1010). Of special interest is the first chapter titled “The Book of Introduction to the Art of Healing”. In this “book”, al-Masihi aims to add and correct already known theoretical medical knowledge, and points out the need for a shorter and simpler presentation of the practical part. The article provides historiographic information to show that al-Masihi’s work was the program and the model for “The Canon of Medicine”, the fundamental and basic work of the great Arab-Islamic physician and polymath Abu Ali Ibn Sina. Having compared the structure and content of these two medical encyclopedic works and considering the historical fact that al-Masihi was a teacher of Avicenna in the art of healing, the author of the article arrives at the conclusion that the treatise “Hundred Books on the Skills of Medicine” could become a forerunner of Ibn Sina’s “Canon of Medicine”. It could be the basis on which the great scientist relied in compiling his fundamental work.