1900. William Orpen (age 21). "The Mirror". Model Emily Scoble from the Slade School of Art tto whom the artist was briefly engaged. She ended their relationship in 1901.

1905. William Orpen (age 26). "The Mirror".

Around 1907. William Orpen (age 28). Portrait of Grace Gifford (age 18).

Grace Gifford: On 03 May 1887 Joseph Plunkett and she were married in the chapel of Kilmainham Gaol, Dublin, a few hours before he was executed. On 04 Mar 1888 she was born. On 13 Dec 1955 she died.

1907. William Orpen (age 28). Self-Portrait. "Self-portrait with glasses".

Around 1908 to 1912. William Orpen (age 29). "Grace reading at Howth Bay". Model the artist's wife [his wife] Grace Knewstub.

Grace Knewstub: After 1901 William Orpen and she were married.

Between 1908 and 1912. William Orpen (age 29). "Grace reading at Howth Bay".

1913. William Orpen (age 34). Self-Portrait. "Sowing New Seed".

1915. William Orpen (age 36). Portrait of Myra Idina Sackville Countess of Erroll (age 21).

1917. William Orpen (age 38). Portrait of Yvonne Aubicq.

1917. William Orpen (age 38). Self-Portrait.

1917. William Orpen (age 38). "The Refugee". Model Yvonne Aubicq".

1917. William Orpen (age 38). Portrait of Lady Marriott, Maud "Momo" Kahn (age 20).

Maud "Momo" Kahn: In 1897 he was born. In 1960 he died.

1918. William Orpen (age 39). "Zonnebeke".

1918. William Orpen (age 39). "Dead Germans in a Trench".

1919. William Orpen (age 40). Portrait of George Allardice 1st Baron Riddell (age 53).

1919. William Orpen (age 40). Portrait of Edgar Gascoyne-Cecil 1st Viscount Cecil (age 54).

1919. William Orpen (age 40). Portrait of Charles Sackville-West 4th Baron Sackville (age 48).

Charles Sackville-West 4th Baron Sackville: On 10 Aug 1870 he was born to William Sackville-West and Georgina Dodwell. On 28 Jan 1928 Lionel Sackville-West 3rd Baron Sackville died. His brother Charles Sackville-West 4th Baron Sackville succeeded 4th Baron Sackville of Knole in Kent. On 08 May 1962 Charles Sackville-West 4th Baron Sackville died. His son Edward Sackville-West 5th Baron Sackville succeeded 5th Baron Sackville of Knole in Kent.

1919. William Orpen (age 40). Portrait of Edward George Villiers Stanley 17th Earl of Derby (age 53).

1928. William Orpen (age 49). Portrait of Ernest Benn 2nd Baronet (age 52).

Ernest Benn 2nd Baronet: On 25 Jun 1875 he was born. On 17 Jan 1954 he died.

1929. William Orpen (age 50). Portrait of Reginald Brabazon 12th Earl of Meath (age 87).

Reginald Brabazon 12th Earl of Meath: On 31 Jul 1841 he was born to William Brabazon 11th Earl of Meath and Harriot Brooke Countess Meath. In 1868 Reginald Brabazon 12th Earl of Meath and Mary Jane Maitland Countess Meath were married. She the daughter of Thomas Maitland 11th Earl Lauderdale. He the son of William Brabazon 11th Earl of Meath and Harriot Brooke Countess Meath. On 26 May 1887 William Brabazon 11th Earl of Meath died. His son Reginald Brabazon 12th Earl of Meath succeeded 12th Earl Meath. Mary Jane Maitland Countess Meath by marriage Countess Meath. On 11 Oct 1929 Reginald Brabazon 12th Earl of Meath died.