The siege of Oldenzaal was a short siege that took place during the Eighty Years' War and the Anglo–Spanish War by a Dutch and English army led by Maurice of Orange of the city of Oldenzaal from 20 to 23 October 1597. The city surrendered to the overwhelming Dutch and English force. The siege was part of Maurice's campaign of 1597 known as the Ten Glory Years, his highly successful offensive against the Spaniards.

The Anglo-Spanish War (1585–1604) was an intermittent conflict between the Habsburg Kingdom of Spain and the Kingdom of England that was never formally declared. It began with England's military expedition in 1585 to what was then the Spanish Netherlands under the command of the Earl of Leicester, in support of the Dutch rebellion against Spanish Habsburg rule.