According to Houbraken, Diepraam first learned to paint from Dirk Stoop's father, who had been a skilled glass painter, and then became an apprentice to Hendrik Martenszoon Sorgh. After travelling through France, he returned to the Netherlands and became an apprentice to Adriaen Brouwer, whose style he copied for the rest of his life. He joined the Guild of Saint Luke in Dordrecht in 1648. Diepraam became a popular painter of small genre works and sold many of them informally in taverns. According to the RKD, Matthijs Wulfraet was his pupil. His paintings were quite popular and generally depict small interior scenes in taverns with farmers drinking or smoking. Houbraken was much more complimentary about Diepraam in his biography of his pupil Wulfraet, claiming that his works sold well in Arnhem and that he was a good teacher for the young boy.