In 1514, Wolsey negotiated a peace treaty with France, which included a marriage alliance between Louis XII and Henry's sister, Mary Tudor.

The Treaty of London in 1518, negotiated by Wolsey, was a significant diplomatic achievement. It was a treaty of perpetual peace signed by England, France, Spain, the Holy Roman Empire, and smaller states.

The Field of Cloth of Gold in 1520 was a grand meeting between Henry VIII and Francis I of France, although it yielded no significant diplomatic achievements.

In 1521, the Treaty of Bruges was signed, forming an anti-French alliance with the Holy Roman Empire.

The Second French War began in 1522, which was costly and yielded little gains.

In 1525, Charles V's victory over the French at the Battle of Pavia led to a shift in the balance of power.

The Treaty of Amiens in 1527 formed an anti-Imperial alliance with France.

In 1532, Henry formed a new, fragile defensive alliance with France.

There were attempts to form an alliance with the League of Schmalkalden to pressure Charles V into supporting Henry's cause.

The Break with Rome occurred in 1533-34, significantly altering England's relationship with Catholic powers in Europe.

In 1536, a major rebellion broke out in Ireland after the dismissal of the Earl of Kildare.

The relationship with Scotland became strained due to religious differences following the Break with Rome.

In 1538, there was a fear of invasion after the Pope's attempt to unite Catholic powers in an anti-English crusade.

Henry VIII married Anne of Cleves in 1540 in an attempt to form an alliance with the League of Schmalkalden, although this marriage was quickly dissolved.

In 1511, Henry joined the Holy League, an anti-French alliance that included Spain, the Holy Roman Empire, England, and the papacy.

War was declared on France in 1512, with Henry sending an army of 10,000 men to southwest France. This campaign resulted in a defeat for the English in Gascony, while Spain's Ferdinand used the opportunity to conquer Navarre.

The year 1513 saw Henry personally leading forces in the Battle of Spurs in France. Although it was little more than a skirmish, it was portrayed as a stunning victory for propaganda purposes.

Henry captured the French towns of Tournai and Thérouanne during this campaign.

While Henry was in France, James IV of Scotland invaded England, leading to the Battle of Flodden. The Scottish king was defeated and killed by a small English army, leaving the Scottish throne to the infant James V.