Manchester United finance director Nick Humby and commercial director Andy Anson have resigned. Humby and Anson, along with chief executive David Gill, are the only non-Glazers heavily involved in the running of United.
The two men helped bridge the gap between the previous plc board and the new ownership structure under American tycoon Malcolm Glazer.
Humby and Anson will leave in February to take up fresh challenges.
Gill admitted he was "very disappointed" at their departure, praising their contribution to the club.
Humby, who joined United in 2002, was responsible for delivering the new stadium expansion on time.
Anson, who arrived in 2004, helped negotiate a record £56.5m shirt sponsorship deal with American banking giant AIG.
Representative of fans' group Manchester United Supporters Trust (MUST) - formerly Shareholders United - who bitterly opposed the Glazer takeover, have urged Humby and Anson to let supporters know what is happening at the club. "Now is the time for them to come clean, do the honourable thing and let the supporters know what is going on behind the scenes at our football club," said MUST spokesman Sean Bones. "At the time of the takeover, Joel Glazer said he would speak to the supporters. They have not done so, which is a shame because we have a lot of questions for them to answer."
The Football365 website reports Capable Hands as saying:
"I am very disappointed to lose Nick and Andy," said Gill.
"Nick has been an excellent finance director at the club for the last five years, getting involved in all areas of the business.
"His final major project has been to manage successfully the stadium expansion in time for the start of the current season.
"In his three years at the club, Andy has set a new commercial strategy on which he has delivered excellently.
"He has played a lead role in our record shirt deal with AIG, as well as the negotiations to restructure our platinum partnerships and media businesses."