Tom Winning was the oldest child of two born to a devout Roman Catholic family in Wishaw, Lanarkshire. His father, the son of an Irish immigrant from County Donegal, had worked as a coal-miner, served in the First World War, and was then employed in the steel industry. On losing his job, his father invested in machinery for making boiled sweets which he sold around the houses in the district as a way of bringing in money for his family. Winning attended St Patrick's Primary, Shieldmuir, Craigneuk. He served as an altar boy and chorister. Then, while at Our Lady's High School, Motherwell, he expressed the desire to become a priest. He successfully applied to study for the Roman Catholic Archdiocese of Glasgow and on acceptance was appointed to St Peter's Seminary, Bearsden, at age 17.
Priesthood
He began training in Saint Mary's College, Blairs, Aberdeen, where philosophy students of St Peter's were temporarily being housed and taught and then moved to St Peter's, Bearsden. When a fire in Bearsden destroyed the seminary during renovation works the entire college community was moved from there to St Joseph's College, Mill Hill, London. After the war ended, he was part of the first group of students to be sent to re-populate the Scots College in Rome. The College had been empty of students since 1939. He was ordained in the Church of St John Lateran, in Rome, on 18 December 1948. His father sold the sweet making machinery as a way to pay the fare for the family to go to Rome for the ceremony. His first appointment was as an assistant at St Aloysius, Chapelhall, Lanarkshire, but after a year he returned to Rome to study Canon Law, gaining in 1953 a Doctorate. Thereafter he was curate in St Mary's Church in Hamilton from 1953 to 1957 and from 1956 secretary to Bishop James Donald Scanlan of Motherwell. After a period in Our Lady of Good Aid Cathedral in Motherwell from 1957 to 1958 he became Chaplain to the Franciscan Sisters of the Immaculate Conception in Bothwell until 1961. At this point he became Spiritual Director at the Pontifical Scots College. Soon after his arrival in Rome, the Second Vatican Council was convened and he was therefore uniquely placed to be involved with the bishops during those historic years of the various Sessions of the Council. At the same time he continued his studies becoming an Advocate of the Sacred Roman Rota in 1965. In the late 1960s, after his return to Scotland, he was appointed minute secretary for the meetings of the Bishops' Conference of Scotland. In 1966 he was called back to Scotland where he was appointed to his first charge as Parish Priest in Saint Luke's, Motherwell, where he remained until 1970 when he was appointed as the first Officialis of the newly formed Scottish National Tribunal.
Episcopate
On 22 October 1971 he was nominated to the episcopacy, as Auxiliary Bishop to the Archbishop of Glasgow, being consecrated Titular Bishop of Lugmad on 30 November 1971 and three years later on 23 April 1974 succeeded Archbishop Scanlan when he was translated to the Metropolitan see of Glasgow. In 1975 he became the first Roman Catholic Archbishop to address the General Assembly of the Church of Scotland in the history of that Church. After his appointment to the College of Cardinals, he was invited once again to address the General Assembly. Winning was often outspoken, and unafraid to publicly expound the Roman Church's understanding of moral matters such as abortion and homosexuality (becoming a supporter of a campaign in 2000, led by businessman Brian Souter, against the repeal of Section 28, and ecclesiastical matters such as the celibacy of priests. He challenged the Act of Settlement. He also began a scheme to give financial support to young mothers, as an alternative to abortion. He rejected a plan to renovate and extend St Andrew's Cathedral, as the money would be better spent on the poor of the Archdiocese. He played a major role in bringing Pope John Paul II to Britain in 1982, a visit that was almost called off because of the Falklands Conflict that coincided with the visit. Winning is thought to have convinced the Pope to continue with the visit which was the first official visit to the United Kingdom by a Pontiff.
Thomas Winning died in office in June 2001, following a heart attack and is interred in the crypt of St Andrew's Cathedral, Glasgow. His successor as Archbishop of Glasgow was Mario Conti. In June 2011, two separate schools in Glasgow combined into one new school located in Tollcross which they voted to call Cardinal Winning after the late Archbishop of Glasgow. The new Cardinal Winning Secondary opened on Tuesday, 21 June 2011 and contains pupils from St Joan of Arc and St Aidan's, two schools located in Glasgow.