The incident happened on a stretch of the notorious Cat and Fiddle road in the Peak District National Park.
Philip Lea Christian, 42, of Buxton, was driving a blue Renault Clio when he hit cyclist Guy Wharton on the A537 Buxton New Road.
Mr Christian was over taking a vehicle, which itself had just overtaken a cyclist on the opposite of the road to Mr Wharton, on a right hand bend. During this manoeuvre the Renault collided with Mr Wharton head on. He died at the scene.
Mr Wharton, 46, was a science teacher at Tytherington School in Macclesfield. He was married with three children.
Mr Christian was cleared of causing death by dangerous driving but pleaded guilty to the charge of causing death by careless driving. Chester Crown Court sentenced him to six months in prison, and banned him from driving for two-and-a-half years. He will also have to undertake an extended retest before he can drive on British roads again.
After the hearing Mr Wharton's widow, Francesca, said:
"We acknowledge the sentencing has been handed down, but it does not change the fact we have been handed a life sentence and have to live every day without a beloved husband and father...
Guy had such a zest for life... loved teaching as well as his cycling and spending time with his family. We continue to miss him dearly."
The Buxton New Road, commonly referred to as "The Cat and Fiddle", after the pub at its summit, is known to be one of the most dangerous stretches of road in the UK.