Harry Cairney's been in charge at Galabank twice, having taken over for the second time in 2006.
He led Annan into the Scottish Football League but now he's decided to step down.
Harry released a statement explaining the pressure of balancing football with his family life and his day job as a teacher was affecting his health.
The Chairman for Annan Athletic, Henry McClelland, paid tribute to the former manager:
Harry Cairney has resigned as manager of Annan Athletic, after six years with the south of Scotland club.
The 51-year-old said that family and health matters, along with a recent spell of bad results were contributing factors in his decision to leave.
– Harry Cairney, former Annan Athletic manager
"In recent times, and I don’t just mean the last month, I have found it very difficult to manage the time I spend with my family, my job and carrying out my duties as Annan Athletic manager.
"The recent run of bad results has not made this any easier and I find myself worrying about football matters when I should be focussing on other areas of my life."
"I would like to thank all players past and present for their efforts on the pitch and on the training ground.
"Thanks, also, to the fans who have faithfully turned up game after game, home and away to cheer the team on."