Despite a successful first season on the pitch (reaching the play-off semi-final and winning the County Cup, under manager Andy Welsh), the club suffered several board resignations and some challenging financial issues.

In November 2019, the club lost a court case, relating to a match in 2015 when Ossett Town played Radcliffe Borough, leaving United facing legal and damages costs of £135,000.

Wayne Benn, assisted by Chick Hayward, had succeeded Welsh as Ossett United manager.

[2] Playing in Division One East in 2021–22, Ossett United were in the top half of the table, but a run of only one win in three months saw a change in the dugout before Christmas 2021,[3] with Jas Colliver and Mark Ward taking a joint managerial role.

Ward resigned in September 2022 with Colliver taking sole charge before leaving the club by mutual consent the following month.

[6] For the remainder of the 23/24 season assistant manager David Brown stepped in as interim manager seeing an upturn in performances on the pitch and in his 20 league games at the helm the side claimed 19 points including five wins to avoid relegation with a game to spare, and ending the season in 16th place.

[8] Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.