Multipolar orderings in degenerate orbital systems offer unique opportunities for emergent topological phases. The phase diagram of interacting spinless fermions in a $p$-band diamond lattice at unit filling is first studied to elucidate the essential role of orbital multipolar orderings in the evolution of multifold degenerate band nodes. The free band structure around the Brillouin zone center is described by two quadratic band nodes each with a threefold degeneracy, which are spanned by the bonding and antibonding $p$-orbital multiplets, respectively. Upon switching on interactions, the triply degenerate band node is split into a pair of Weyl fermions with opposite chirality due to the onset of orbital multipolar orderings. Further raising interactions ultimately drives the system into an insulating phase with the orbital quadrupolar ordering. Our study is then generalized to spin-$\frac{1}{2}$ fermions, which has direct relevance with solid-state materials. The system develops full spin polarization through a ferromagnetic transition at tiny interactions, leaving the remaining orbital sector activated. The ensuing transitions take place in the orbital sector as a natural consequence, qualitatively recovering the phase diagram of spinless fermions. Our findings shed light on the realization of emergent fermions with a prospect being a frontier at the confluence of topology, orbital physics, and strong correlation.