Feisal Nahaboo, who is a member at East Berkshire Golf Club, in Ravenswood Avenue, played 18 holes on 18 different courses in one day against former England striker Alan Shearer.
Mr Nahaboo, who lives near the golf course, came up with the challenge – which took place on Monday – to raise money for the Alan Shearer Foundation, which supports disabled children and adults.
The pair began their epic journey at Mr Shearer’s local club in Close House in Northumberland, before playing their 17th hole at Blue Mountain golf course in Binfield, and the last at East Berkshire.
Mr Nahaboo said: “I’m delighted that Alan took on this fun challenge to benefit his charity. I tried to create the ultimate golfing challenge – a round of golf, played within daylight hours, on courses spanning the country, from Newcastle to Crowthorne with 16 other courses in between.
“We travelled by any means we could – train, helicopters and road to cover the distance between holes.”
Mr Shearer, now a BBC television football pundit, said he had played golf for a number of years but “never like this."
He beat Mr Nahaboo in their match by two holes.
At each course, two other people joined the pairing to play a hole. At East Berkshire Golf Club, one man was given a dream birthday present when he won the chance to play.
Alan Davison, 69, won the opportunity after his wife entered his name into a tombola at the club and he was drawn out of the hat on his birthday on Sunday.
The Newcastle United supporter was then watched by by his wife June and his four grandchildren the following day.
Mr Davison said: “It was exciting. There were quite a few people there and I was shaking like a leaf because the fairways were lined with people. I’ve been playing golf for a long time but it’s clearly one of the highlights.”
Mr Davison, from Finchamp-stead, said Mr Shearer was an “amazing golfer” but managed to draw the hole on handicap with the ex-England man.
He said: “I’ve been a lifelong Newcastle fan and a Shearer fan after he appeared on the scene. He was very charming and very pleasant, very good with everyone. He was very good company and stayed around afterwards.
“I was walking down the fairway and he was chatting about games he’d played and I’d watched. It was a great birthday present.”