[5] Association football was introduced to Workington in the 1860s and further popularised when a group of steel workers migrated to the town from Dronfield, Derbyshire.

were one of the founder members of the Cumberland Association League in 1888 and played at the Ashfield Ground before moving to Lonsdale Park for the 1909–1910 season.

During the 1933–34 season, the club managed its best-ever FA Cup performance, reaching the 4th round, before losing to Preston North End.

[15] During the 1957–58 season they played the great Manchester United team known as the Busby Babes at home in the 3rd round of the FA Cup, attracting a record crowd of 21,000.

The club's proudest night was at Blackburn Rovers on 22 October 1964 in a Football League Cup 3rd round replay.

This was reported in one newspaper as "Incredible Fantastic Workington rubbed Rovers elegant noses in the mud of Ewood Park to produce the finest result in their 80 year history"[22] On 3 April 1965, Workington gave a debut to one of the youngest players ever to play in the Football League, Tony Geidmintis, who was only 15 years 247 days old.

This was Peter Foley, who played over 80 games for Workington as a forward and scored some 16 goals for the club, before moving on to Scunthorpe where he kept a young Kevin Keegan out of the team for a couple of years.

Manager Ken Furphy had moved on to Watford, taking some of Workington's key players such as Dave Carr and Dixie Hale with him.

In the 1968–69 season Workington gave a Football League debut to one of the game's legendary goalkeepers, John Burridge.

A cult hero at the club, Martin was often dubbed the "poor man's George Best",[27] but to older supporters with longer memories, his tricks were reminiscent of the Clown Prince of Football Len Shackleton.

The club's appearance record for the whole period that Workington played in the Football League was achieved by Bobby Brown.

[33] Brown, who was selected for the Third Division North representative team while at Workington, made a total of 469 league and cup appearances for the club between 1956 and 1967.

On 10 February 1978 a special fundraising friendly game was organised at Borough Park which saw two of the World's greatest ever players gracing the Workington pitch.

On that night a Workington team, captained by Sir Bobby Charlton took on Fort Lauderdale Strikers (a touring side from the USA) who had Gordon Banks keeping goal.

The game was watched by a crowd of 6,127 who witnessed a fantastic 25 yard strike by Charlton which was only matched by the quality of the save by Banks.

[35] The club was in poor financial straits with debts of £300,000, but on 9 April 1986 George Best played for the "Reds" in a fund-raising friendly match against a Lancashire Football League 11.

The Oldham Athletic chairman, Ian Stott, put together a team managed by Joe Royle to play at Borough Park.

Hence a few weeks before Best's fortieth birthday he captained the Workington team with Phil Neal leading out the opposition, which included players from Oldham Athletic, Carlisle United and Bolton Wanderers.

2009-2010 Promotion Play Off Disappointment After two mid table finishes the following seasons, Workington made the playoffs again, this time going down 4–1 on aggregate to Alfreton Town in the semi-final.

Skelton left Workington in June 2015 to take a coaching role with the Dumfries club Queen of the South.

2015-2016 Promotion Play Off Disappointment Workington qualified for their second successive Northern Premier League Play-off beating Blyth Spartans 4–3 in the semi-final before going down 2–3 in the final against Salford City 2016-2017 Promotion Play Off Disappointment On 19 April 2017, having beaten Ilkeston 2–0, Workington qualified for their third successive Northern Premier League playoff losing 2–3 in the semi-final against Stourbridge after extra time.

2017–2018 After a slow start to the season the side went on a 17 match unbeaten run to sit 2nd in the Northern Premier League table at the turn of the year.

Manager Chris Willcock left at the end of the season and was replaced was Danny Grainger who commenced his second managerial spell with the club.

2022-2023 Promotion back to Northern Premier League Reds lost many players before the season started and August 2023 saw some disjointed performances.

The Reds wrapped up a successful season by winning the Cumberland County Cup in style, beating Penrith 9–1 in the final.