On 30 Apr 1565 Robert "The Elder" Peake (age 14) commenced his training under Laurence Woodham at the Sign of "The Key" Goldsmith's Row Cheapside.

On 20 May 1576 Robert "The Elder" Peake (age 25) became a Freeman of the Worshipful Company of Goldsmiths.

After 20 May 1576 Robert "The Elder" Peake (age 25) was in the pay of the Master of the Revels.

In 1582 Robert "The Elder" Peake (age 31). Portrait of Anne Knollys Baroness De La Warr (age 26).

Anne Knollys Baroness De La Warr: On 19 Jun 1555 she was born to Francis Knollys and Catherine Carey. On 19 Nov 1571 Thomas West 2nd Baron De La Warr and she were married. On 30 Dec 1595 William West 1st Baron De La Warr died. His son Thomas West 2nd Baron De La Warr succeeded 2nd Baron De La Warr. She by marriage Baroness De La Warr. On 30 Aug 1608 Anne Knollys Baroness De La Warr died.

In 1590 Robert "The Elder" Peake (age 39). Portrait of Katherine Carey Countess Nottingham (age 40).

Around 1590. Robert "The Elder" Peake (age 39). Portrait of Elizabeth Oldenburg (age 16).

Elizabeth Oldenburg: On 25 Aug 1573 she was born to Frederick II King Denmark and Sophie Mecklenburg-Schwerin Queen Consort Denmark. On 19 Apr 1590 Henry Julius Duke of Brunswick-Lüneburg and she were married. She the daughter of Frederick II King Denmark and Sophie Mecklenburg-Schwerin Queen Consort Denmark. On 19 Jun 1625 Elizabeth Oldenburg died.

Around 1597 Robert "The Elder" Peake (age 46). Portrait of Peregrine Bertie 13th Baron Willoughby (age 41).

In 1605 Robert "The Elder" Peake (age 54). Portrait of Arabella Stewart (age 30).

In 1608 Robert "The Elder" Peake (age 57). Portrait of Elizabeth D'Oyly née Knightley.

On 14 Oct 1608 Robert "The Elder" Peake (age 57) was paid £7 for "pictures made by His Highness' (age 14) command".

On 14 Jul 1609 Robert "The Elder" Peake (age 58) was paid £3 "for a picture of His Highness (age 15) which was given in exchange for the King's picture".

In 1610 Robert "The Elder" Peake (age 59). Portrait of Princess Elizabeth Stewart Queen Bohemia (age 13).

In 1611 Robert "The Elder" Peake (age 60). Portrait of King Charles I of England, Scotland and Ireland (age 10) in his Garter Robes and Leg Garter.

In 1611 Robert "The Elder" Peake (age 60). Portrait of Elizabeth Watson Lady Penyston (age 11). She is wearing a draped mantle-embroidered with seed pearls in a pattern of ostrich plumes-and a matching turban. The mantle knotted on one shoulder was worn in Jacobean court masques.

In 1611 Robert "The Elder" Peake (age 60) and Paul Isackson painted the cabins, carvings, and armorials on the ship the Prince Royal.

On 10 Jul 1613 Robert "The Elder" Peake (age 62) was paid £13.6s.8d. by the vice-chancellor of the University of Cambridge, "in full satisfaction for Prince Charles (age 12) his picture", for a full-length portrait which is still in the Cambridge University Library.

In 1616 Robert "The Elder" Peake (age 65). Portrait of (possibly) Frances Cotton (age 38).

Frances Cotton: In 1578 she was born to Thomas Cotton and Elizabeth Shirley. On 24 Feb 1612 Edward Montagu 1st Baron Montagu and she were married at Weekley, Northamptonshire. In May 1620 Frances Cotton died.

Before 1619 Robert "The Elder" Peake (age 68). Portrait of Anne Vavasour (age 58).

Before 1619 Robert "The Elder" Peake (age 68). Portrait of William Pope 1st Earl Downe (age 45).

Before 1619 Robert "The Elder" Peake (age 68). Portrait of Henry Frederick Stewart Prince of Wales in his Garter Robes and Leg Garter.

In 1619 Robert "The Elder" Peake (age 68). Portrait of Vere Egerton (age 23).

Vere Egerton: Around 1596 she was born to Thomas Egerton and Isabella Venables. In 1619 William Booth and she were married. On 05 Apr 1629 or 04 May 1629 Vere Egerton died. She was buried at Booth Chapel.

On 10 Oct 1619 Robert "The Elder" Peake (age 68) made his will.

On 16 Oct 1619 the will of Robert "The Elder" Peake (deceased) was proved.