1868 – He was born on August 23 of this year in Garnett, Kansas, where his father had briefly moved to set up a law practice.
1880 – His family moved to Lewistown, Illinois, where he attended high school and had his first publication in the Chicago Daily News.
1889 – He attended The Knox Academy from this year until 1890. A defunct preparatory program run by Knox College, but was forced to leave due to his family's inability to finance his education.
1898 - He married Helen M. Jenkins, the daughter of a lawyer in Chicago, and had three children. He published several other volumes of poems including Book of Verses in this year.
1903 – During his law partnership with Clarence Darrow, from this year until 1908, Masters defended the poor.
1911 – He started his own law firm, despite the three years of unrest (1908-1911) due to extramarital affairs and an argument with Darrow.
1914 – He truly began developing as a notable American poet, when he began submitting a series of poems (this time under the pseudonym Webster Ford) about his childhood experiences in Western Illinois, which was published in Reedy's Mirror, a St. Louis publication.
1915 – His series was bound into a volume and re-titled Spoon River Anthology.
1936 – He was awarded the Mark Twain Silver Medal this year.
1941 – He was awarded at the Poetry Society of America medal in this year.
1942 – He was awarded at the Academy of American Poets Fellowship.
1944 – He received an award in the Shelly Memorial Award in this year.
1950 – He died March 5 of this year. He was buried in Oakland cemetery in Petersburg, Illinois.
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