In Lord Caitanya Mahaprabhu's final pastimes, both Ramananda Raya and Svarupa Damodara always engaged in reciting suitable verses from Srimad-Bhagavatam to pacify the Lord's ecstatic feelings of separation from Krsna. It is said that when Lord Caitanya went to southern India, Sarvabhauma Bhattacarya advised Him to meet Ramananda Raya, declaring that there was no devotee as advanced in understanding the conjugal love of Krsna and the gopis. While touring South India, Lord Caitanya met Ramananda Raya by the bank of the Godavari, and in their long discourses the Lord took the position of a student, and Ramananda Raya instructed Him. Caitanya Mahaprabhu concluded these discourses by saying, "My dear Ramananda Raya, both you and I are madmen, and therefore we met intimately on an equal level." Lord Caitanya advised Ramananda Raya to resign from his government post and come back to Jagannatha Puri to live with Him. Although Sri Caitanya Mahaprabhu refused to see Maharaja Prataparudra because he was a king, Ramananda Raya, by a Vaisnava scheme, arranged a meeting between the Lord and the King. This is described in the Madhya-lila, Chapter Twelve, verses 41-57. Sri Ramananda Raya was present during the water sports of the Lord after the Ratha-yatra festival.

Lord Sri Caitanya Mahaprabhu considered Sri Ramananda Raya and Sri Sanatana Gosvami to be equal in their renunciation, for although Sri Ramananda Raya was a grhastha engaged in government service and Sri Sanatana Gosvami was in the renounced order of complete detachment from material activities, they were both servants of the Supreme Personality of Godhead who kept Krsna in the center of all their activities. Sri Ramananda Raya was one of the three and a half personalities with whom Sri Caitanya Mahaprabhu discussed the most confidential topics of Krsna consciousness. Lord Caitanya Mahaprabhu advised Pradyumna Misra to learn the science of Krsna from Sri Ramananda Raya. As Subala always assisted Krsna in His dealings with Radharani in krsna-lila, so Ramananda Raya assisted Lord Caitanya Mahaprabhu in His feelings of separation from Krsna. Sri Ramananda Raya was the author of Jagannatha-vallabha-nataka.