<p style='text-indent:20px;'>The Bose-Hubbard dimer model is a celebrated fundamental quantum mechanical model that accounts for the dynamics of bosons at two interacting sites. It has been realized experimentally by two coupled, driven and lossy photonic crystal nanocavities, which are optical devices that operate with only a few hundred photons due to their extremely small size. Our work focuses on characterizing the different dynamics that arise in the semiclassical approximation of such driven-dissipative photonic Bose-Hubbard dimers. Mathematically, this system is a four-dimensional autonomous vector field that describes two specific coupled oscillators, where both the amplitude and the phase are important. We perform a bifurcation analysis of this system to identify regions of different behavior as the pump power <inline-formula><tex-math id="M2">\begin{document}$ f $\end{document}</tex-math></inline-formula> and the detuning <inline-formula><tex-math id="M3">\begin{document}$ \delta $\end{document}</tex-math></inline-formula> of the driving signal are varied, for the case of fixed positive coupling. The bifurcation diagram in the <inline-formula><tex-math id="M4">\begin{document}$ (f, \delta) $\end{document}</tex-math></inline-formula>-plane is organized by two points of codimension-two bifurcations——a <inline-formula><tex-math id="M5">\begin{document}$ \mathbb{Z}_2 $\end{document}</tex-math></inline-formula>-equivariant homoclinic flip bifurcation and a Bykov T-point——and provides a roadmap for the observable dynamics, including different types of chaotic behavior. To illustrate the overall structure and different accumulation processes of bifurcation curves and associated regions, our bifurcation analysis is complemented by the computation of kneading invariants and of maximum Lyapunov exponents in the <inline-formula><tex-math id="M6">\begin{document}$ (f, \delta) $\end{document}</tex-math></inline-formula>-plane. The bifurcation diagram displays a menagerie of dynamical behavior and offers insights into the theory of global bifurcations in a four-dimensional phase space, including novel bifurcation phenomena such as degenerate singular heteroclinic cycles.</p>