The masterpiece poetic book “Gulshan-i Raz” was composed by Sheikh Mahmoud Shabestari (687–720 AH) during the 8^th century AH responding the fifteen questions received by him. The work was fundamentally focus on Wahdat al-Wujud and appeared as comprehensive thesis of Sufi thought and teaching. The work emerged during the transition era; the Islamic world was experiencing a period of gradual cultural decline, while the religious tolerance of the Ilkhanate era had simultaneously diminished the influence of Sunni Islam and emboldened alternative sects and Sufism. Centuries later, Allama Muhammad Iqbal Lahori (1294–1357 AH) penned Gulshan-i Raz-i Jadid. His era significantly resembled with Shabestari time. In an effort of revitalizing self-confidence and dignity of the muslim, and to restore the spiritual and religious values of the East in the face of the challenges posed by modernity by West, Iqbal introduced his philosophy of Khudi. This is the fundamental difference between the viewpoints and methods of Shabestari and Iqbal. As a result, Iqbal offered fresh responses to a number of Shabestari's original queries. Three main thematic axes—self-knowledge, the relationship between the part and the whole, and the conflict between unity and plurality—are used in this article to compare and contrast the perspectives of these two thinkers.