While comparing handwritings of two different sets, the conventional method is to compare the class and individual characteristics. The class characteristics of two or more persons may show similarities but on the basis of similarities of class characteristics alone no final opinion of identity can be given unless it is followed by the comparison of most individual writing characteristics. However, in some rare instances it is exceptionally seen that even the most individual characteristics were concretely found similar, may be co-incidentally, in the handwritings of two different individuals. The present study is based on observations on handwritings of two great personalities Mahatma Gandhi and Sh. Rabindra Nath Tagore. Such findings being so rare and surprising need further analysis as to what could be the cause of such coincidental similarities of individual characteristics in the handwriting of two different persons. Such findings appear slightly contradictory to the well established principles of significance of individual characteristics.