The North American (NOAM) plate converges with the Caribbean (CARIB) plate at a rate of 20.0 ± 0.4 mm/yr. towards 254 ± 1°. Plate convergence is highly oblique (20–10°), resulting in a complex crustal boundary with along-strike segmentation, strain partitioning and microplate tectonics. We study the oblique convergence of the NOAM and CARIB plates between southeastern Cuba to northern Puerto Rico using new swath multibeam bathymetry data and 2D multi-channel seismic profiles. The combined interpretation of marine geophysical data with the seismicity and geodetic data from public databases allow us to perform a regional scale analysis of the shallower structure, the seismotectonics and the slab geometry along the plate boundary. Due to differential rollback between the NOAM oceanic crust north of Puerto Rico and the relative thicker Bahamas Carbonate Province crust north of Hispaniola a slab tear is created at 68.5°W. The northern margin of Puerto Rico records the oblique high-dip subduction and rollback of the NOAM plate below the island arc. Those processes have resulted in a forearc transpressive tectonics (without strain partitioning), controlled by the Septentrional-Oriente Fault Zone (SOFZ) and the Bunce Fault Zone (BFZ). Meanwhile, in the northern margin of Hispaniola, the collision of the Bahamas Carbonate Province results in high plate coupling with strain partitioning: SOFZ and Northern Hispaniola Deformed Belt (NHDB). In the northern Haitian margin, compression is still relevant since seismicity is mostly associated with the deformation front, whereas strike slip earthquakes are hardly anecdotal. Although in Hispaniola intermediate-depth seismicity should disappear, diffuse intermediate-depth hypocenter remains evidencing the presence of remnant NOAM subducted slab below central and western Hispaniola. Results of this study improve our understanding of the active tectonics in the NE Caribbean that it is the base for future assessment studies on seismic and tsunamigenic hazard.