Former studies carried out in the 2000s in the Lahn-Dill region located in the middle-east of the German state Hesse stated a depletion of arable weeds on the field scale and more diverse weed flora on the landscape scale. Current study, having started in 2018, aims to contribute to a better understanding of the interactions between arable weed species diversity, farming intensity, grown crops and landscape area. Moreover, the potential of organic farming methods for conservation and promotion the arable weed diversity is aimed to be assessed with the study. In total, 42 fields in two landscape regions were sampled—six seedbank samples were collected from each field; additionally, data on spontaneous arable weed flora were recorded each spring from 2019 to 2021; emerged aboveground weeds were identified in the fields and their coverage was documented. Four factors were considered in the field trial: Farming practice, landscape area, soil depth and the current crop. Effects of these factors on arable weed species diversity were calculated with a Generalized Linear Model (GLM), resulting in significant effects of the management system, the area and the current crop. Among the four organic farming systems that were sampled, the time period of organic growing had a significant effect on weed seed numbers in the soil with an increase in seed numbers. Average seedbank species numbers were around twice as high in organic farming systems (18 species) compared to conventional managed fields (nine species). Evidence of an ongoing species decline in the region on the landscape scale could be detected by comparison with a former study. Especially rare and endangered weed species are a concern due to seedbank and current vegetation depletion tendencies.