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.
"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."
Annan Athletic have been thrown out of the Scottish FA Youth Cup after admitting an error with the registration of three players who played in their 2-1 win over Montrose in the last Round.
The Third Division side held their hands up to the SFA upon learning that three youngsters from their under-16 side had not been properly registered to play in the under-20 tournament.
Now they have stepped aside rather than get involved in a lengthy debate which allows Montrose time to prepare for their match against Dunfermline in the fourth round.
Annan chairman Henry McClelland said:
“There has been an administrative error on our part that we have admitted to. It is a really sore blow for the boys and the club but something that we will learn from and it will not happen again.”
“We could have appealed but that would not have been the right thing to do as we had made a mistake and it would not have been fair to keep Montrose hanging around.”
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Work is getting under way on a £592,000 project to install an artificial pitch at the home of Scottish 3rd Division football side Annan Athletic. The finance for the "third generation" surface includes money seized from criminals in the Scottish government's Cashback for Communities scheme.
It's hoped the pitch will be ready for the start of the new season. Funding has also come from Dumfries and Galloway Council and Sport Scotland.
Part of the 3G development involves levelling off the slope at the Galabank ground. Club chairman Henry McClelland said that would involve a huge effort.
"Essentially what will happen, at the top end of the park the pitch will be lowered by two feet and at the bottom it will be raised by two feet. The time frame is very tight. Our first scheduled game in the Ramsdens Challenge Cup could be a home tie on the last Saturday in July. The likelihood of completion for that date is very, very tight."
If it is not ready, Mr McClelland said the Scottish Football League would allow them to play their first two ties away from home, if necessary.