Active Galactic Nuclei (AGN) outflows can regulate host galaxy evolution via AGN feedback. Ionised gas outflows have been linked to enhanced radio emission. In the first paper of this series, AGN detected with the International LOFAR Telescope (ILT) at 6" were more likely to host an [OIII] 5007{AA} outflow than AGN not detected, although only high-powered jets were ruled out as the origin of radio emission. New wide-field, sub-arcsecond resolution imaging at 144 MHz with the ILT now enables a resolved morphological study of this sample. We present the first wide-field, sub-arcsecond images of the Bootes Deep Field at 144 MHz, detecting 4074 sources in the ~0.3" image with a central sensitivity of 33.8uJy/beam. For 47 AGN matched in AGN luminosity, we probe radio emission on kiloparsec-scales to investigate correlations with [OIII] outflows. This sample spans z<0.83, 10^40^<L[OIII]<10^43^erg/s, and 10^21^<L144MHz<10^24.5^W/Hz. We find that if we detect an AGN on both large-scales (6") and small-scales (0.3"), 90+/-7 per cent have an [O III] outflow, compared to 63+/-9 per cent of sources detected on large-scales, but undetected on small-scales. Furthermore, 17+/-6 per cent of sources without an [OIII] outflow are detected on kiloparsec-scales, compared to 51+/-12 per cent of sources with an [OIII] outflow. This implies a connection between [OIII] outflows and kiloparsec-scale radio emission, which is likely AGN-driven. In contrast, AGN without an [OIII] outflow are dominated by diffuse radio emission, likely to be associated with star formation.