In this paper, we construct and classify a new family of flips, called generalized Grassmannian flips, by generalizing the construction of standard flips for $\mathbb{P}^m\times \mathbb{P}^n$ to any generalized Grassmannian $G/P$, where $P$ is a maximal parabolic subgroup of a complex semi-simple algebraic group. In addition, we show that a 9-fold generalized Grassmannian flip for $Sp(6, \mathbb{C})$ satisfies the DK flip conjecture by Bondal-Orlov and Kawamata via mutation techniques by Kuznetsov and Thomas' chess game method.