Low-dimensional ferroelectricity and Dirac materials with protected band crossings are fascinating research subjects. Based on first-principles calculations, we predict the coexistence of spontaneous in-plane polarization and novel 2D emergent fermions in dynamically stable quadruple-layer (QL) XSbO$_2$ (X= Li, Na). Depending on the different polarization configurations, QL-XSbO$_2$ can exhibit unconventional inner-QL ferroelectricity and antiferroelectricity. Both ground states harbor robust ferroelectricity with enhanced spontaneous polarization of 0.56 nC/m and 0.39 nC/m for QL-LiSbO$_2$ and QL-NaSbO$_2$, respectively. Interestingly, the QL-LiSbO$_2$ possesses two other metastable ferroelectric (FE) phases, demonstrating the first 2D example with multiple FE orders. The ground FE phase can be flexibly driven into one of the two metastable FE phases and then into the antiferroelectric (AFE) phase. During this phase transition, several types of 2D fermions emerge, for instance, hourglass hybrid and type-II Weyl loops in the ground FE phase, type-II Weyl fermions in the metastable FE phase, and type-II Dirac fermions in the AFE phase. These 2D fermions are robust under spin-orbit coupling. Notably, two of these fermions, e.g., an hourglass hybrid or type-II Weyl loop, have not been observed before. Our findings identify QL-XSbO$_2$ as a unique platform for studying 2D ferroelectricity relating to 2D emergent fermions.