In the 12th and 13th centuries, Guelders quickly expanded downstream along the sides of the Maas, Rhine, and IJssel rivers and even claimed the succession in the Duchy of Limburg, until it lost the 1288 Battle of Worringen against Berg and Brabant.

On separate occasions, in return for loans from the treasury of Guelders, the bishop of Utrecht granted the taxation and administration of the Veluwe, and William II – Count of both Holland and Zeeland, and who was elected anti-king of the Holy Roman Empire (1248–1256) – similarly granted the same rights over Nijmegen; as neither ruler proved able to repay their debts, these lands became integral parts of Guelders.

[citation needed] In 1339, the Emperor Louis IV of Wittelsbach elevated Count Reginald II of Guelders (also styled Rainald), of the House of Wassenberg, to the rank of Duke.

Subsequently, Guelders was ruled by Habsburg Holy Roman Emperor Maximilian I, husband of Charles the Bold's daughter and heir, Mary.

Following in the footsteps of Charles of Egmond, Duke William formed an alliance with France, an alliance dubiously cemented via his political marriage to French King Francis I's niece Jeanne d'Albret (who reportedly had to be whipped into submission to the marriage,[1] and later bodily carried to the altar by the Constable of France, Anne de Montmorency).

[2][3] This alliance emboldened William to challenge Emperor Charles V's claim to Guelders, but the French, mightily engaged on multiple fronts as they were in the long struggle to against the Habsburg "encirclement" of France, proved less reliable than the Duke's ambitions required, and he was unable to hold on to the duchy; in 1543, by the terms of the Treaty of Venlo, Duke William conceded the Duchy of Guelders to the Emperor.

William Thatcher, the lead character in the 2001 film A Knight's Tale played by Heath Ledger, claimed to be Sir Ulrich von Liechtenstein from Gelderland to appear to be of noble birth and thus qualify to participate in jousting.

Set in the late 1460s, the main character in Rafael Sabatini's 1929 novel The Romantic Prince is Count Anthony of Guelders, elder son of Duke Arnold and brother to Adolf "since then happily vanished".