In the early part of the 19th century, the Mathews family ran a successful business in St. Giles, Oxford. William, the father, was an engraver, while his son Michael Angelo was a stationer and artist’s colourman.

Lacking his father's talent as an engraver, Michael Angelo turned his attention to the insurance business, which was then just beginning. In the early days, insurance operated through an agency system, with local businessmen using their connections to place insurance with the companies they represented.

Looking for an agency with a life assurance office and being a life-long abstainer, Michael Angelo chose to work with the United Kingdom Temperance and General Provident Institution, taking out his first policy in 1851. Becoming a full-time insurance intermediary in Oxford was a bold step in those days. Although insurance agents, or brokers, were found in the major shipping and industrial cities of London and Liverpool, the same opportunities did not exist in a university city.

Described by one of his contemporaries as a man of 'integrity, industry and persistence', Michael Angelo had a genuine desire to serve mankind in a new and useful way, and the insurance side of the business flourished. He was soon joined by his son, Angelo, and in 1880 the business moved to 6 St. Aldate's in Oxford city centre, where it remains to this day.

In 1899, his youngest son, Wilfrid, aged just sixteen, joined the company, taking advantage of Oxford's early industrial growth and expanding the business steadily. Taking a keen interest in motoring in its early days, he opened the first office of the Automobile Association at 6 St. Aldate's, and remained with the company for sixty-four years.

In 1947, John Comfort joined Wilfred, having worked in insurance before the war and deciding he would enjoy greater freedom as a broker rather than with an insurance company. The business grew rapidly and in 1968 changed its name to Mathews Comfort & Company in recognition of his influence. In the years that followed, Mathews Comfort continued to provide independent insurance advice and financial services, launching Mathews Comfort Financial Services as a separate company in 1988.

In 1999, the company became a founder member of the Willis Commercial Network (today known as Willis Towers Watson Networks), giving customers the benefit of global resources alongside local, independent, professional advice.

In December 2017, J Bennett & Son, an independent insurance broker established in 1908, acquired Mathews Comfort, sharing the same approach and core values, making for the perfect marriage and offering a combined heritage of 275 years.