After the collapse of the permanent signing of on-loan striker Christian Doidge, Forest Green Rovers commenced legal action over lost earnings.

[3] In February 2019, Bolton were issued a winding-up petition by HM Revenue & Customs (HMRC) which was subsequently adjourned, first until April, and then again until the end of the season as their search for a new owner continued.

[4][5] Due to the financial difficulties, the training ground temporarily closed in March 2019,[6] and games against Ipswich, Middlesbrough and Aston Villa were threatened with postponement or being played behind closed doors as the local council Safety Advisory Group (SAG) threatened to revoke the stadium safety certificate.

[7] The Bolton Whites Hotel, owned by Ken Anderson, was also issued with a winding-up petition in March 2019[8] (it closed on 1 May and went into administration on 14 May).

[13] Fildraw (former owner Eddie Davies' trust fund) appointed administrators from insolvency firm David Rubin and Partners.

Pre-season friendlies with Chester,[17] Preston[18] and Oldham Athletic were all cancelled as Bolton could not give assurances about fielding a competitive team.

Bolton started their opening League One game on 3 August at Wycombe Wanderers with only three contracted senior outfield players, and lost 2–0.

[23] On 10 August, Bolton fielded its youngest ever side, with an average age of 19, in a goalless home draw against Coventry City,[24] but then conceded five goals in both of the next two games, against Rochdale in the EFL Cup (5-2)[25] and Tranmere Rovers in League One (5-0).

[37] On 28 August, Bolton announced that the club's sale to Football Ventures (Whites) Limited had been completed, with the administrator paying tribute to the Eddie Davies Trust and their legal team, and criticising Anderson who had "used his position as a secured creditor to hamper and frustrate any deal that did not benefit him or suit his purposes.

"[38] On 31 August, shortly after Bolton lost a fourth consecutive game conceding five goals in each, Keith Hill was announced as the new club manager.

Like the season before against St Mirren, the Bolton first team refused to play the match against Chester due to unpaid wages.