Former Arsenal winger Marc Overmars will leave his role with Ajax with immediate effect after the Eredivisie side said he had sent "a series of inappropriate messages to several female colleagues".
The Dutchman, who had been the club's director of football affairs for just under ten years, decided to step down from his role following talks with the club's board, as well as chief executive and Manchester United icon Edwin van der Sar.
A statement from Ajax read: "Director of Football Affairs Marc Overmars will leave Ajax with immediate effect.
"He made this decision after discussions in recent days with the Supervisory Board and CEO Edwin van der Sar and communicated his intentions to them.
"A series of inappropriate messages sent to several female colleagues over an extended period of time underlies his decision to leave the club."
Overmars himself condemned his own actions, admitting he was ashamed of his behaviour.
"I am ashamed. Last week I was confronted with reports about my behaviour", he said.
"And how this has come across to others. Unfortunately, I didn't realize that I was crossing the line with this, but that was made clear to me in recent days. I suddenly felt enormous pressure.
"I apologize. Certainly, for someone in my position, this behaviour is unacceptable. I now see that too. But it is too late. I see no other option but to leave Ajax.
"This also has a major impact on my private situation. That is why I ask everyone to leave me and my family alone."
Ajax Supervisory Board chairman Leen Meijaard admitted that it was a 'devastating' situation for the women subject of Overmars' behaviour, claiming that Overmars continuing with the club wasn't an option.
Meijaard said: "This is a dramatic situation for everyone who is involved in any way.
"It is devastating for the women who have had to deal with the behaviour. When we heard news of this, we immediately acted, carefully deliberating and weighing what was the best thing to do - all in consultation with CEO Edwin van der Sar and assisted by an external expert.
"Marc is probably the best football director that Ajax has had. We upgraded and extended his contract for a reason. But, unfortunately, he has really gone over the line, so continuing as director was not an option, as he recognized himself.
"It is extremely painful for everyone. I want to express the wish that everyone involved is given the peace and privacy to process this."
