One of its best periods was immediately before the Second World War; when Ollerton Colliery reached three Notts Senior Cup finals in a row from 1936 to 1939, winning it in 1937/38.

In 1930, a side called Ollerton Forest defeated Welbeck Athletic 3–0 in the North Notts Senior Cup final at Mansfield Town's Field Mill stadium.

[1] After the resignation of Don Gethfield back in 2011, and a brief stint under Paul Rawden, the club appointed Dave Winter as first team manager, with Stephen Bodle as his assistant.

The former Kirkby Town pair guided the club to the Central Midlands Floodlit Cup final in their first season.

In the 2015–16 season, with former-captain Jamie Allan now also on board as first team coach, the club secured promotion to the Northern Counties East League after finishing runners-up in the Central Midlands North Division.

The club topped the division after 12 games, winning 9 of them, but the season was brought to a premature end due to the Coronavirus pandemic.