The scarcity of water resources is one of the main barriers to further food production. On the other hand, the historical evaluation of food production systems regarding crop water productivity is a key factor in understanding the country’s food security. Thus, this manuscript describes the historical development of water productivity components, along with water stress and imported food, in the Gulf Cooperation Countries (GCCs) of Bahrain, Kuwait, Oman, Qatar, Kingdom of Saudi Arabia (KSA), and the United Arab Emirates (UAE) from 2000 to 2020. This is to highlight the vulnerability of the GCCs food supply to overseas water use in imported food. Water productivity is calculated based on Gross Domestic Product (GDP) per cubic meter of total freshwater withdrawal. The annual freshwater withdrawal refers to the withdrawal from storage basins, desalination plants, and non-renewable aquifers, and also includes the withdrawal for agriculture and livestock. The review analysis is based on the Food and Agriculture Organization (FAO), AQUASTAT data, the World Bank, the Organisation for Economic Co-operation and Development (OECD) for GDP estimates, and the World Research Institute-Aqueduct. The results revealed that between 2000 and 2020, the annual freshwater withdrawals for livestock and crops dropped by 20.8%. The cereal production harvested for dry grain also dropped by about 36% between 2000 and 2020. The decrease in water withdrawals and cereal production has not affected water productivity, where it has increased, growing at an average rate of 121.8% from 92.8 in 2000 to 205.9 in 2020. The increase in livestock production index (meat, milk, cheese, eggs, honey, raw silk, wool, hides, and skins) by about 189% between 2000 and 2020 could be the main reason for improving water productivity. Therefore, livestock production is the most crucial component of agriculture in GCCs, contributing the biggest percentage of water productivity. As a result, the food imports were 11.3% as a share percent of total merchandise imports. This percentage is equivalent to 90% of the food demand in the GCCs, meaning an increase in water imported in agricultural products. This research highlighted that despite the improvements in water productivity, the GCCs are not self-sufficient in food, as about 90% of GCCs food demand is imported, and consequently, the impact on water use and productivity is overseas. Hence, it is important to understand, and account for, the impact of imported food on water productivity overseas. In the future, funders are recommended to make greater engagements with international organizations concerned with agriculture and water use to promote sustainable production chains between both GCCs and the countries to which food is imported; water security perspectives.