Millwall FC struck gold with combined £2.5m expense on Barnsley and Sheffield United transfers | OneFootball

Millwall raided Yorkshire clubs with loan-to-buy deals that more than paid off

Not every transfer window can be a winner for clubs in the EFL, but the summer transfer window back in 2018 will be looked upon fondly by Millwall fans for the arrivals of Tom Bradshaw and Ryan Leonard.

The Lions broke their transfer record twice to bring the pair to South London, where they enjoyed fruitful spells.

Millwall signed both players on initial loan deals in August 2018, with the pair becoming permanent members of the squad at the Den the following January, midway through the 2018/2019 Championship season.

Tom Bradshaw

Welsh international swapped Yorkshire for London by becoming Millwall’s first £1million+ player

Strikers can be worth their weight in gold at any level of the footballing pyramid, so it is no surprise that most clubs are willing to spend most of their money on securing goalscorers.

That is exactly what the Lions planned when they brought Bradshaw down south from Barnsley midway through August 2018, with the former Aberystwyth Town striker signing on an initial loan.

Although officially an undisclosed fee was paid for the forward, it was confirmed by the club that it had broken the previous record fee paid by Millwall.

That record had stood for almost 30 years, with the Lions paying Derby County £800,000 for striker Paul Goddard in 1989.

Previous record-holder Goddard only managed two goals in 17 appearances for Millwall, whereas Bradshaw managed to plunder 45 goals in 211 matches for the Lions.

Sky Sports reported at the time that the move was in excess of a million pounds, making Bradshaw the first player in Millwall history to cost the club a seven-figure fee.

Millwall even managed to recoup some of their transfer fee when the now 32-year-old Bradshaw departed in January 2025 for divisional rivals Oxford United, linking back up with former Lions boss Gary Rowett.

Ironically, Bradshaw's final appearance in a Millwall shirt came away at Oxford United on New Year's Day.

Ryan Leonard

He is still going strong for Millwall seven years in

Bradshaw only spent a few weeks as Millwall’s most expensive signing, with the capture of Ryan Leonard breaking the record once again.

Signed right at the end of August 2018, Leonard’s move shared a lot of similarities with Bradshaw.

Not only was the deal also an initial loan with a guarantee of a permanent move in the following January transfer window, but it also saw Leonard swap Yorkshire for London.

Leonard had only been at Sheffield United for half a season before the Blades decided to sanction his departure, paving the way for his move to Millwall.

After joining on loan at the Den, Leonard would cost the Lions a potential £1.5million in a permanent move.

Fast-forward seven seasons later, and Leonard is still a regular first-team player for Millwall.

Capable of playing in midfield or at right-back, Leonard has made over 190 appearances for the Lions.

A fan favourite at the Den, Leonard was named player of the season at the end of the 2023/24 Championship campaign.