Madonna's record label Maverick has lost $66m (£37m) since 1999, according to court documents filed by its parent company Warner Music.
Madonna is signed to Warner Music as a solo artist
The recently unsealed documents are the latest twist in an ongoing dispute between the pop star and the company.
Madonna is suing Warner Music for $200m (£112.5m), claiming its mismanagement and improper accounting has cost her and her partners millions of dollars.
Maverick's line-up of artists include Alanis Morissette and Michelle Branch.
According to trade paper Hollywood Reporter, the documents form part of a pre-emptive claim in which Warner Music asserts it has fulfilled its commitment to Madonna's record label.
The "sealed lawsuit" was filed in a Delaware court on 24 March - one day before Madonna lodged her legal action in Los Angeles Superior Court.
Subsequently unsealed, the documents claim Madonna must pay $92.5m (£52m) - in addition to the value of Warner's interest in Maverick - in order to terminate its agreement with the parent company.
The $92.5m includes the $66m incurred in losses, a $20m (£11.2m) loan and $6.5m (£3.6m) in unpaid fees
Alanis Morissette releases her new album in May
Warner Music say that if the money is not forthcoming, it can legitimately convert Maverick into a "purely passive economic interest".
If this were to happen, Warner would take control of the label and Maverick would receive no share of the profits until the losses were repaid.
The issue is further complicated by the fact that Madonna is also signed to Warner as a solo artist, and begins a world tour in May.
Another factor is the imminent release of Morissette's first album in two years, So-Called Chaos.
Warner Music has called Maverick's accusations "baseless, unsubstantiated and without merit", but has attempted to distance the action from its other dealings with Madonna.
"This effort to resolve ongoing contractual issues surrounding the Maverick Records joint venture agreement in no way impacts the company's deep respect for Madonna," it said in a statement released last month.
Madonna and business partners Guy Oseary and Ronnie Dashev - who have a 60 per cent stake in Maverick - seek to end the label's partnership with Warner Music so they can collaborate with other companies.