Berry phase effect plays a central role in many mesoscale condensed matter and quantum chemical systems that are naturally under the environmental influence of dissipation. We propose and microscopically derive a prototypical quantum coherent tunneling model around a monopole or conical potential intersection in order to address the intriguing but overlooked interplay between dissipation and topologically nontrivial Berry phase effect. We adopt the instanton approach with both symmetry analysis and accurate numerical solutions that consistently incorporate nonperturbative dissipation and Berry phase. It reveals a novel dissipative quantum interference phenomenon with Berry phase effect. The phase diagram of this tunneling exhibits Kramers degeneracy, nonmonotonic dependence on dissipation and a generic dissipation-driven phase transition of quantum interference, before which an unconventional dissipation-enhanced regime of quantum tunneling persists.