Winifred Gleeson was one of the four children of Winifred Moloughney and Thomas Gleeson. Winifred and her first husband, William Whelan, had arrived in South Australia from Tipperary, Ireland in 1851 on board the ship Catherine as free immigrants. They later moved to the goldfields in Bendigo. William Whelan died there in 1854. In 1855 Winifred married Thomas Gleeson in Bendigo. Thomas had arrived in Van Diemen's Land on the Kinnear in 1842 and now held a conditional pardon. In 1856 Thomas moved his new family, which included two step-children, to Tasmania and settled at Dry Creek, near New Norfolk. In 1862 tragedy struck again when Thomas died as the result of an accident.

Winifred struggled to provide for her family after her husband's death. In October 1862 she made an application for admission of three of her children to the Queen's Orphan School (SWD 26/5). The children were Catherine Gleeson (Whelan) who became Orphan 2076 and 5612, Thomas Gleeson (Orphan 2080) and Winifred (Orphan 2082). The older children were admitted on 15 October and Winifred, who was recorded as five years and four months of age, was admitted to the Infants School on the following day. She remained there until November 1863, when she was transferred to the (Upper) Female School (SWD6, page 25).  Winifred remained there until 1868 when she was discharged to the care of her mother. Her brother, Thomas, was discharged on the same day. Their mother, now settled at Lachlan, New Norfolk, had married for the third time to John McRedmond in 1864.

In May 1872, Winifred Gleeson and her brother Thomas were witnesses at the marriage of their half-sister, Catherine Whelan, to William Briers. She was a witness once more when Thomas married Harriet Eliza Brooks in 1876. Winifred and her sister, Johannah Gleeson, married two brothers, Thomas and William Mitchell, in 1883 and 1884. Winifred had a large family and has many living descendants.