Background
Gregory was born in Pinner in 1886. The second of six sons, Gregory was named after his father, who was a tenant farmer at Pinner Hill Farm, and later the licensee of Oddfellows public in Pinner.
Gregory was born in Pinner in 1886. The second of six sons, Gregory was named after his father, who was a tenant farmer at Pinner Hill Farm, and later the licensee of Oddfellows public in Pinner.
He was educated at Pinner National School, and played his first game of men"s football aged 11, for Pinner Football Club"s reserves.
He played for, initially as an inside forward, and latterly as a half back and full back. In his early adult years, his primary sporting focus was cricket. He played as a batsman for Pinner Central Committee and Eastcote Central Committee, before coaching the Benskins Brewery cricket team
Gregory joined as an amateur in 1911, turning professional later the same year.
At one stage, all four of them were contracted to the club simultaneously, although only Fred and Val went on to play for the first-team He went on to play every game in October and November, and was still in the team when Val made his debut on 25 December, in a 1–1 draw at home to Luton Town.
Fred continued to play on a regular basis from then on, and finished his first season with 25 appearances and 8 goals in all competitions, as the club finished 9th. Over the following two seasons he continued to play regularly, but the team dropped 14th in the 1912-1913 season, and narrowly avoided relegation in 1913-1914 with an 18th-placed finish.
Despite Britain"s participation in the First World War, the 1914-1915 season continued as scheduled.
As a result of the war, peacetime competitions were suspended from 1915 until 1919. Gregory served in the Royal Garrison Artillery, but also made 53 appearances for in wartime fixtures. On the resumption of peacetime football in 1919-1920, Gregory played 34 league games.
, along with all other Southern League First Division clubs, joined the newly formed Football League Third Division in 1920.
The team finished the season in 6th position, with Gregory making 21 league appearances. Over the next five seasons, Gregory continued to play frequently, making at least 20 appearances per season as a left back, and regularly attracting praise from journalists covering "s opposition.
However, his professional career ended in a 6–1 defeat at Exeter City, on 1 May 1926. Although he ultimately did not make another first-team appearance, Gregory remained at for a further two seasons, and made several appearances for the reserves.
He became landlord of The Victory public in Pinner in 1926, a role that he continued for the remainder of his life.
In his later years he suffered from tuberculosis, and he spent the final four months of his life at a sanatorium in Harefield. Gregory died on 24 May 1937, aged 50.
Came close to defending their title, but eventually missed out to Portsmouth on the final day of the season on goal average.