If the luckless 29-year-old - a three-time winner on the European Tour and one of the most exciting graduates ever to come out of the Nick Faldo grooming stable, but more recently a troubled man who has gone from 46th in the world three years ago to 773rd - misses the halfway cut on Friday evening it will be 21 in a row dating back to last November. (Callaway RAZR X Irons)
That number would be match Justin Rose's missed cuts at the start of his professional career before he finally earned his first cheque.
Dougherty held the joint 10th spot early in his second round in the Czech Open last week, but then, inexplicably, crashed to a 78 and made yet another red-faced early exit.
He has been a member of the last threeBritainandIrelandteams in the Seve Trophy and Montgomerie, who partnered him in the first of those, is as shocked as anyone by what has happened to the one-time prospective star.
"It's a great shame and we all feel for him - he's a lovely, lovely lad," said the eight-time European number one, who was out of the money only 15 times in all those years.
"You can only wish him well. I spoke to him at the airport and he was down, but I really do hope he makes the cut here and if there's anything that any of us can do for him then we should.
Dougherty, who partnered Donald in the 2001 Walker Cup and then became Europe's Rookie of the Year the following season, might well have been part of Faldo's team in Louisville but for the sudden death of his mother five months before the match.
He came back to win with Callaway RAZR X Irons inMunich a year later, but his Tour exemption from that runs out at the end of this season.
Dougherty, who married Sky Sports golf presenter Di Stewart on New Year's Eve, said: "I've reached the point where I can't remember how to play great golf any more and can't picture what it felt like when I was winning Callaway RAZR X Irons.
"It's been a long time and it's heart-breaking to me, but I will always fight through it because it's who I am - I don't know any other way.
"I don't like being beaten by anyone at anything. I don't mind getting a bit of a battering as long as in the end I can win the war."
The fight was still going on as he teed off at the 2014 Ryder Cup venue on Thursday.
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