After a brief existence in the South Holderness League, like many of its contemporaries The Eastenders moved to the East Riding County League on the demise of the former competition in 1954. For many of the next fifty years, the club hovered around the bottom tier, with just the occasional promotion and cup run offering a hint at better times.
In 1990/91, under legendary manager Mike Wilson, Easington won the Division 3 title, their first ever divisional championship. They also came very close to a league and cup double but fell short in the final of the Harold Robinson (League) Cup.
Wilson's team continued its upward progress, eventually attaining Premier Division status for the first time in 1999/00. They did so on the back of a memorable 1998/99 campaign in which the club lifted the East Riding Intermediate Cup, courtesy of a 5-0 win over AFC Darleys at Dene Park.
In the summer of 2000, Easington United became founder members of the Humber Premier League (FA Supply League) and due to the work put in to meet the entry criteria, they were given the honour of participating in the competition's inaugural match, at Hall Road Rangers Reserves on 16th August.
Ridiculed in some quarters for accepting the membership offer, The Eastenders initially struggled to find their feet in the new competition. Gradual improvement followed and in his final season in charge 2002/03, Wilson's side achieved a top five finish as well as reaching the semi-finals of the East Riding Senior Cup (for the third year running) and semi-finals of the League Cup. In addition, they continued their dominance of local football with victory in both the South Holderness Cup and at the Withernsea Carnival.
Mike Wilson's successor Sean McLaughlin took things on one step further and in 2003/04 United finished runners-up to HPL champions Hutton Cranswick United. In the event they were left to rue a poor October for costing them the title. Despite their disappointment the team consoled themselves with victory in the League Cup, achieved on penalties over Bridlington Town Reserves in an exciting final at Pocklington. Four wins in as many matches over perennial 'top dogs' Reckitts, a Holderness double trophy haul, a share of the HPL 'Team of the Year' award and a 'Golden Boot' for leading scorer Paul Wilkinson completed a memorable campaign.
During this period, Easington became the team to beat locally with eight South Holderness Cup successes in eleven years as well as victory over Hornsea Town in 2007's inaugural Holderness Cup Winners Cup. It was a feat they would repeat in 2012.
Dave Mackay-Dundas succeeded Sean McLaughlin in 2005/06 and oversaw the rebuilding of the team. In the summer of 2009, after an excellent fourth placed finish in the HPL, The Eastenders made the move to the Central Midlands Football League for season 2009/10.
A promising first season saw the locals just miss out on promotion from the Premier Division to the Supreme Division. However, following regionalisation (to North and South Divisions) the club struggled, usually finishing in the bottom third of the North table. In 2012/13 Sean McLaughlin returned to take the management reins for a second time. However, after initial promise he couldn't repeat his earlier success and was replaced by former club captain Andy Graham. Graham was supported by Paul Wilkinson and player/coach Andy Martin but tragedy struck in November 2015 when the latter passed away after a short illness.
Amid another disappointing campaign and with reported mounting disquiet at League Committee level about the club's continued membership, the decision was taken in January 2016 to return to local football and the Eastenders were accepted back into the Humber Premier League for 2016/17.
An awful first season back saw United relegated to Division 1 for 2017/18. Therein an influx of players from ER County League side Patrington saw the team recover from a slow start to achieve a creditable 6th place finish. In addition they enjoyed a fine run to the semi-finals of the East Riding Senior Country Cup, beating Scarborough League side Goal Sports and fellow HPL Division 1 teams Blackburn Athletic and Howden Amateurs along the way. Sadly, they produced a poor performance in the semi-final, eventually going down on penalties to eventual cup winners Pocklington Town Reserves, after neither side had managed to score in 120 minutes football.
The end of the 2017/18 campaign also brought the curtain down on Andy Graham's time as manager. Following his decision to step down, Adam Jamieson was appointed player/manager for 2018/19, assisted by coach Luke Jeffery and former manager Dave Mackay-Dundas.
At the end of the 2018/19 season, in which the Eastenders again reached the last four of the East Riding Senior Country Cup only to lose out on penalties, this time to eventual runners-up Blackburn Athletic, Adam also decided to relinquish the role and return solely to a playing remit for 2019/20. He has been succeeded by Danny Blount, appointed player/manager in June and assisted by the club's record goalscorer Craig Foster. Luke Jeffery stayed on in a coaching role but Dave Mackay-Dundas stepped down from his matchday duties due to increasing work commitments.