[21] On October 2, 1892, Charles Winchester was killed after an explosion in his hotel after he was spraying a room for bedbugs,[22][23] and is interred at the Yankton City Cemetery.

The Beulah Christian reported in March 1902 that on one occasion "Sister Olive Winchester, a member of this church, and senior at Radcliffe College, spoke at the morning service with special unction.

[24] According to Nazarene historian Stan Ingersol, Winchester's Harvard instructor in Semitic languages regarded her as "a student of exceptional ability.

In 1909 Winchester broke a gender barrier as the first woman matriculated into the Bachelor of Divinity course at the University of Glasgow.

"[28] During this time Winchester won the Cook and McFarlan Testimonial Prize of £21,[38] awarded annually since 1847 in memory of Duncan Macfarlan, DD, Principal of the University of Glasgow (1823 to 1858), and George Cook, DD, Professor of Moral Philosophy in the University of St Andrews, to "the most distinguished candidate in Greek, Moral Philosophy, Hebrew, Ecclesiastical History and Divinity.

[40] On April 30, 1910, Winchester departed from Glasgow on the S.S. Cassandra, and subsequently arrived in Quebec, Canada on May 10, 1910, en route to the USA.

[60] For several years Winchester wrote to the leaders of the Pentecostal Church of the Nazarene in Kansas City, Missouri, urging them to send representatives to Scotland to expedite a merger of the two denominations.

[70][71] Additionally, Winchester was the beneficiary of 25% of a substantial estate of her maternal great-uncle, Levi Merrick Stewart (December 10, 1827, in Corinna, Maine – May 3, 1910, in Minneapolis, Minnesota).

She spurred further interest in that emerging discipline by contributing frequent articles on religious education to church papers and curriculum resource manuals.

... A history of Northwest's first quarter-century summarized her administrative role in a sentence: "She contributed very much to the development of the right attitude toward scholastic standards, as vice-president and dean of the college had much to do with the internal organization of the institution."...

At the center of her legacy stood the undeniable fact that she was a pivotal figure in the transition of Northwest Nazarene College from a sagebrush academy to a sound academic institution.

"[78] In June 1932 Olive Winchester attended the Eighth General Assembly of the Church of the Nazarene in Wichita, Kansas, as a delegate from the Idaho-Oregon District.

[79] Winchester resigned from Northwest Nazarene College in 1935 due to differences with Wiley's successor, President Russell V. DeLong.

Wiley invited her to teach at Pasadena College (now Point Loma Nazarene University) where she taught until her death in 1947.

While at Pasadena College, Winchester served as one of the advisors for the Revised Standard Version of New Testament,[80] that was published on February 11, 1946.

[87] According to Ingersol, "Winchester had earned high marks in biblical criticism at Glasgow but was conservative in her application of this knowledge within the Nazarene context.

Her Crisis Experiences in the Greek New Testament (1953) stood in the linguistic-exegetical tradition pioneered by Daniel Steele, a Methodist scholar at Boston University.

Steele defended the doctrine of entire sanctification by a study of the Greek aorist, and Winchester appropriated his agenda and attempted to develop it further, though this approach has since fallen out of favor with many Wesleyan-holiness biblical scholars.

[88]However, Nazarene theologian and general superintendent John A. Knight argued in 1995 that Winchester and Steele were part of an "earlier generation of holiness-traditions scholars [who] overstated the grammatical evidence for entire sanctification as a 'second definite work of grace.

Reflecting the New England tradition of Wesleyan-holiness biblical scholarship shaped by Daniel Steele, she was amillennial and interpreted the Book of Revelation as a coded record of events that had occurred in the New Testament era, perhaps during Nero's reign, not predictions of the future.

[85] In 1931, Winchester wrote a series on science and religion in The Young People's Journal, a Nazarene publication for high school youth, where she had a regular column.

The Olive Winchester Memorial Church of the Nazarene in the upper terraces of La Paz, Bolivia has ministered to the Aymara since 1960 is named in her honor.

[92] On May 8, 2012, John Mason MSP Scottish National Party for Glasgow Shettleston moved that the following be entered into the record of the Parliament of Scotland: "Parliament notes that 11 May 2012 is the 100th anniversary of the first woman being ordained to the UK Trinitarian Christian Ministry; considers that Olive Winchester, who was ordained to, and served in, what is now the Sharpe Memorial Church of the Nazarene, Parkhead, Glasgow, set a precedent for strong women of faith to serve in Christian ministry; notes the Women in Ministry events being held in Glasgow between 11 and 13 May 2012, including those at the University of Glasgow; believes that every woman, child and man is of equal value, and wishes the organisers and people taking part well as they celebrate what it believes is this significant milestone for the UK's Christian community.

[96][97] A commemorative service was held on the evening of May 11, 2012, in Sharpe Memorial Church of the Nazarene at Parkhead, where Winchester was ordained.