The Anglo-Scottish Wars comprise the various battles which continued to be fought between the Kingdom of England and the Kingdom of Scotland from the time of the Wars of Independence in the early 14th century through to the latter years of the 16th century.

Although the Wars of Independence, in which Scotland twice resisted attempted conquest by Plantagenet kings of England, formally ended in the treaties of 1328 and 1357 respectively, relations between the two countries remained uneasy. Incursions by English kings into Scotland continued under Richard II and Henry IV and informal cross-border conflict remained endemic. Formal flashpoints on the border included places remaining under English occupation, such as Roxburgh Castle and the port of Berwick-upon-Tweed. Roxburgh was recaptured by the Scots in 1460 under Mary of Guelders after the death of James II in the same campaign. Similarly, they captured Berwick in 1461 in exchange for support to the Lancastrians. Berwick had changed hands a number of times in the past, and as one country attempted to take advantage of weakness or instability in the other, siding on one side in the civil war, culminating in final capture for the English of the Scottish port by the Yorkist Richard, Duke of Gloucester in 1482.

England's preoccupation with civil war during the Wars of the Roses and Scotland's aid to the Lancastrian cause may have been a component in the period of relative recovery for her northern neighbour during the course of the 15th century, and by the first decade of the 16th century James IV of Scotland and Henry VII of England were making overtures for lasting peace after aiding the latter, along with Scotland's ally France in the Battle of Bosworth. This broke down after the accession of the more overtly bellicose Henry VIII to the English throne and James IV's catastrophically misjudged incursion into Northumbria in 1513 ending in the Battle of Flodden. Three decades later, after the death of James V in 1542, the so-called 'rough wooing' at the hands of invading English armies under the Earl of Hertford brought manifest depredations to Scotland. The last pitched battle between Scotland and England as independent states was the Battle of Pinkie on September 10, 1547. Periods of fighting and conflict nevertheless continued.

France also played a key role throughout the period of the Anglo-Scottish Wars. Scots and English soldiers on French soil during the Hundred Years' War (1337–1453) generally fought on opposing sides, with the Scots standing for the French against the English under the Auld Alliance. France in later periods, in turn, often intervened on Scottish soil for the Scots. This French involvement had increasingly complex political consequences for all sides by the later 16th century.

The Anglo-Scottish Wars can be said to have formally ended with the Union of the Crowns in 1603, wherein England and Scotland entered a personal union under James VI and I, who inherited both crowns. Bloody conflict between the two states nevertheless continued to arise in different and more complex guise throughout the course of the 17th century.

During the mid-15th century, there were many conflicts on the border of England and Scotland, most notably the Battle of Sark in 1448. These battles were the result of England's ongoing military campaigning in France and Scottish attempts to support the House of Valois.

During the English invasion in 1482, an army led by Richard, Duke of Gloucester captured Berwick-upon-Tweed in 1482 and continued to Edinburgh. Berwick has remained English since then.

England under Henry VIII declared war on France in 1512 (as part of the larger conflict known as the War of the League of Cambrai). James IV of Scotland invaded England in fulfillment of his alliance with France (even though married to Henry's sister Margaret). In 1513, after preliminary raids by borderers came to grief, James's main army invaded England. His artillery quickly subdued English castles such as Norham and Wark. However, James issued a formal challenge for an open field battle to the English army under the Earl of Surrey and then fortified his position; this perceived lack of chivalry led Surrey to warn James that no quarter would be given or accepted. Surrey's army manoeuvred around the Scottish army, which launched an attack to open a route north to Scotland. In the resulting disastrous Battle of Flodden, James IV was killed, along with many of his nobles and gentry, the "Flowers of the Forest".