Sufficient freshwater is needed for water dependent sectors such as agriculture, nature, drinking water, and industry. However, even in low-lying, flood prone countries like the Netherlands, climate change, weather extremes, economic growth, urbanization, land subsidence and increased food production will make it more complex to guarantee sufficient freshwater for all sectors. Furthermore, the frequency and amplitude of extremely dry and wet weather conditions is expected to increase. The current Dutch water management system is not designed to anticipate these extremes. Over the last decades, drained Dutch agricultural fields, land consolidation and urbanization resulted in declining groundwater tables. Additionally, the fresh water demand of different sectors (agriculture, industry, drinking water) increased, causing an increased pressure on the regional groundwater system. As a consequence, the annual groundwater table in sandy soil areas dropped over time with the effect that, nowadays, fresh water is becoming scarce in dry periods. In this paper we provide insight in the shifting water management strategy in the Netherlands (1950–2020), with the corresponding drainage systems, developing from conventional drainage (approx. 1950–1990), to controlled drainage (1990’s onwards), climate adaptive drainage (2010 onwards) and subirrigation systems (2018 onwards). Furthermore, we provide insight in the effect of subirrigation on groundwater levels and crop yields, based on both international literature and measurements of Dutch field pilots. Although subirrigation can contribute to improved soil moisture conditions for crop growth on field scale, we show that the water volume needed for subirrigation can be large and could put a significant pressure on the available regional water sources. Therefore, efficient and responsible use of the available external water sources for subirrigation (e.g. surface water, treated waste water, or groundwater) is required. Finally, the implementation of controlled drainage with subirrigation asks for correct implementation in the regional balance: it requires an integral, catchment-wide approach.