At the start of the period, concurrent with the accession of Henry IV (r. 1399–1413), England's first Lancastrian king, Great Britain and Ireland are rife with internal tensions, including Welsh revolt, a series of baronial rebellions led by the Percy family of Northumberland, and ongoing warfare among the Anglo-Irish nobility. In 1415, Henry V (r. 1413–22) renews the war with France that has continued, with interruptions, for nearly a century. His endeavors are temporarily successful, gaining large territories in France and securing his claim to the French throne. During the reign of his son Henry VI (1422–61; 1470–71), however, the English are expelled from France with the help of Joan of Arc, a French peasant girl, and political turmoil erupts at home when the king's frequent illnesses place England in the hands of a Protector, Richard, duke of York. By the end of the fifteenth century, civil war between the Yorkists and Lancastrians seriously undermines the power of the monarchy and leaves the nobility fractured and vulnerable to the prevailing Tudor family.

The sixteenth century witnesses both a dramatic shift of power in the hands of the increasingly autocratic English monarch, and the emergence of England as a major presence in international commerce. Tensions between England and Wales are relieved by the Act of Union in 1536, and Tudor rulers tighten their control in Ireland, particularly after the religious upheaval at mid-century. Irish civil wars continue to rage, however, and culminate at the turn of the seventeenth century. Scotland, facing similar civil unrest in the fifteenth century, forges an alliance with France through the marriage of James V to Marie of Guise (1515–1560) and earns the enmity of England. The conversion of Scotland to Protestantism, led by John Knox (1513–1572), repairs the rift.

In 1534, seventeen years after Luther initiates the Reformation in Germany, Henry VIII (r. 1509–47) severs his own ties with the Catholic Church. He establishes the Church of England, and effects a religious reformation shortly to be undone by his Catholic daughter, Mary I (r. 1553–58), but upheld by her successor, Elizabeth I (r. 1558–1603). Elizabeth's reign marks a turning point in the economic and artistic life of the British Isles; by her death in 1603, England is the center of a rich literary culture and, with its powerful navy, maintains numerous trading interests in Europe and the East and claims in the New World.

• 1401–1415 Welsh lord Owen Glendower (1359?–1416?) leads a revolt, ultimately unsuccessful, against British rule in Wales.

• 1453 The Hundred Years' War, a series of military conflicts beginning in 1337 over English dynastic claims to the throne of France, ends in the defeat of English forces. Of the considerable territories won by England in the preceding century, encompassing most of France north of the Loire, all but Calais are restored to French authority.

• 1455 The Wars of the Roses erupt between the houses of Lancaster and York, two branches of the ruling Plantagenet dynasty. Richard (1411–1460), duke of York and Protector of England, attempts to depose the ailing Lancastrian king Henry VI. Civil war ensues, and in 1461 Richard's son is crowned Edward IV (r. 1461–70, 1471–83).

• 1476 William Caxton (ca. 1421–1491) sets up a printing press at Westminster, and in the following year produces Dictes and Sayenges of the Phylosophers, the first dated book to be printed in England. Among other works, many of which he translates and edits himself, Caxton prints two editions of Chaucer's Canterbury Tales, Sir Thomas Malory's Morte Darthur (1485), and The Myrrour of the Worlde (1481), a popular science handbook.

• 1485 Henry Tudor defeats the army of King Richard III (r. 1483–85) at the Battle of Bosworth and claims the throne, ending the Wars of the Roses. Henry VII (r. 1485–1509) consolidates the power of the monarch and reduces the authority of an already weakened nobility by reviving the Court of the Star Chamber, for the trial of unlawful barons, in 1487.

• 1494 Poynings' Law is passed in Ireland, subjecting all Irish Parliaments to the jurisdiction of the English Privy Council. By this act, Henry VII curtails the rights of Irish subjects.

• 16th century Painting in miniature, or "limning," is an esteemed art form of the period. Portrait miniatures painted on vellum or card, frequently encased in elaborate gold and jeweled frames, are worn as pendants or brooches, or decorate small boxes. Hans Holbein the Younger (1497/98–1543) produces miniatures in London during the reign of Henry VIII, and his work is admired by Nicholas Hilliard (ca. 1547–1619), the most celebrated artist at the court of Elizabeth I. Hilliard explains the intricacies of his craft in his treatise of about 1600, the Arte of Limning.

• 1515/17 Henry VIII establishes the Royal Workshops for armor production at Greenwich. The armor manufactured there reflects the combined influence of Flemish and German craftsmen, headed by Martyn van Royne (active 1515–40).

• 1516 Sir Thomas More (1478–1535), a statesman in the service of Henry VIII, publishes Utopia, an essay on the ideal state, containing a satirical commentary on contemporary political corruption and social imbalances. Along with his friend Erasmus of Rotterdam (ca. 1466–1536), More is a central figure of the humanist movement active in sixteenth-century Britain.

• 1526 German painter Hans Holbein the Younger visits England, later settling in London in 1532. During his first visit, he executes portraits of Sir Thomas More and other nobles in the circle of Henry VIII. Holbein's later patrons include German merchants of the Hanseatic League and, by 1537, the king himself. Under Henry VIII, Holbein not only produces portraits of the royal family and the king's prospective brides, but also designs jewelry, plate, state robes, and other decorative objects for the royal household.

• 1533 Anxious for a male heir, Henry VIII annuls his marriage to Catherine of Aragon, marries Anne Boleyn and, later that year, Princess Elizabeth (later Queen Elizabeth I) is born. For this act, Henry is excommunicated by the pope.

• 1534 Parliament passes the Act of Supremacy, establishing the Church of England and declaring that the English monarch is its head and protector. Subjects are required to swear an oath of loyalty and reject papal authority; some leading churchmen who refuse the oath, including former chancellor Sir Thomas More, are put to death.

• 1536 The Act of Union between England and Wales is passed; Wales rapidly assimilates English law.

• 1536–1539 Thomas Cromwell (ca. 1485–1540), vicar-general to Henry VIII, supervises the dissolution of monasteries and convents suspected of corruption, seizes monastic property, and issues injunctions against the worship of images and the sale of relics.

• 1549 Parliament passes the First Act of Uniformity, proclaiming the Roman Catholic mass illegal. Church interiors are whitewashed and religious images are removed from view. Thomas Cranmer (1489–1556), archbishop of Canterbury, compiles the First Book of Common Prayer, and church services are for the first time conducted in English instead of Latin.

• mid-16th century Henry VIII undertakes the expansion of two palaces seized from Cardinal Thomas Wolsey (ca. 1473–1530)—Whitehall and Hampton Court—and, shortly thereafter, begins the construction of Nonsuch Palace. This surge of architectural activity emphasizes the role of the court as a seat of political and administrative power.

• mid-16th century–1600 Thomas Tallis (ca. 1505–1585) and William Byrd (1540–1623) are the leading composers of the period. Both serve as organists in the Chapel Royal, and in 1575 are jointly granted by Elizabeth the monopoly of publishing music. In that year they publish a collection of motets (polyphonic choral works), the Cantiones sacrae.

• 1553 Mary Tudor, daughter of Henry VIII and Catherine of Aragon, accedes to the throne upon the death of her fifteen-year-old half-brother, Edward VI (r. 1547–53). A fervent Catholic, Mary I (r. 1553–58) restores papal supremacy in England and puts many Protestants to death, including three bishops in 1555 and Archbishop Cranmer in 1556 (thus earning the name "Bloody Mary").

• 1558 Elizabeth (r. 1558–1603), daughter of Henry VIII and Anne Boleyn, accedes to the throne. Acts of Supremacy and Uniformity passed in this year reinstate Anglicanism and affirm Elizabeth's role as head of the Church of England. Elizabeth's reign is marked by a flourishing of the arts, particularly literature and drama, and the rise of England as a major sea power.

• 1560 Scotland is declared a Protestant nation. Seven years later, the Catholic Mary, Queen of Scots, is forced to abdicate and flees to England. Queen Elizabeth imprisons her, and twenty years later warrants her execution. Mary's Protestant son James VI (later James I of England) is crowned upon her abdication in 1567.

• 1572 Parliament licenses theatrical troupes, an important advance toward the professionalism of theatrical activity and the promotion of secular drama. Four years later, James Burbage builds The Theatre, the first permanent playhouse in London. By the end of the century, London's theatrical world is dominated by two great rival troupes: the Lord Admiral's Men, managed by Philip Henslowe and led by playwright Christopher Marlowe and actor Edward Alleyne, and the Chamberlain's Men, co-owned by Richard Burbage and William Shakespeare. The Chamberlain's Men ultimately prevail, winning the patronage of James I in 1603.

• 1588 Spanish monarch Philip II sends the Armada, a fleet of 130 ships, to England in an attempt to overthrow Elizabeth. Her navy attacks the Armada while it is anchored near Calais and forces it to disperse; many of the ships that manage to survive are destroyed by storms. This significant English victory ends the threat of Spanish commercial supremacy and domination of the Atlantic, encouraging British interests in the New World.