Allama Shibli Naomani is commonly known as a loyal colleage of Sir Syed Ahmed Khan but some disagreements also existed between them. These debates became general after the publication of 'Hayat e Shibli' in 1943. In this book, the biographer Syed Sulaiman Nadwi concluded that Shibli left Aligarh because of Sir Syed. He also described the tense relationship between these two legends. These claims were rejected by Sir Syedians and a chain of writings came into existence discussing Shibli's disloyalty. In this article, this conflict is reconsidered from a new perspective, providing facts to better understand the issue. Furthermore a comprehensive study of the friendly relationship between these two legends has also been presented here, focusing on the forward to Shibli's book 'Al-Mamoon'.