During a period where Woods reigned supreme over the golf world winning 74 US Tour titles, including 14 Majors, he has been unable to extend his dominance to the biennial competition that pits the US's best against Europe's best.
A mediocre 13-14-2 mark from six Ryder Cups does not enhance the brilliance resume of Woods, who has been able to celebrate just one team win from six Ryder Cup appearances.
Woods's struggles have coincided with lean times for the US with Europe hoisting the Cup in six of the last eight events.
"Well, certainly I am responsible for that because I didn't earn the points that I was put out there for," Woods said. "I believe I was out there, what, in five sessions each time and I didn't go 5-0 on our side.
"So I certainly am a part of that and that's part of being a team. I needed to go get my points for my team and I didn't do that.
"Hopefully I can do that this week, and hopefully the other guys can do the same and we can get this thing rolling."
Medinah Country Club, which will serve as the scene for this week's 39th US-Europe showdown, represents a great chance for Woods to improve his record.
Medinah has been a happy hunting ground for the 36-year-old American, who picked up two of his 14 Majors at the stately tree-lined layout with victories at the 1999 and 2006 PGA Championships.
"I've always loved coming here," said Woods, who is also a five-time winner of the PGA Tour event at nearby Cog Hill. "I enjoy playing in Chicago and for some reason, I've just had a lot of success here.
"I don't know what it is but I seem to be very, very comfortable here."
There have been differing theories behind why Woods has not been able to impose his will on the Ryder Cup in the same fashion he has been able to in PGA Tour events.
Graeme McDowell, a U.S. Open winner and three-time member of the European team, believes that for much of Woods's career he has played with a target on his back. The same bull's-eye current world number one Rory McIlroy will have painted on his golf shirt this week.
"I kind of liken it to playing premiership football, the biggest teams, the Manchester Uniteds, the Liverpools, the Chelseas, the Arsenals," explained McDowell.
"Any lesser team that comes to play these guys, they have a tendency to raise their game because it's a huge game for an underdog to play a Tiger Woods.
"They get up for it. They are not expected to win."
Finding the right playing partner for Woods, who is back close to his best form winning three PGA Tour events this year, has always proven a bit of puzzle for U.S. captains.
His singles record of 4-1-1 is impressive, but he does not play well with others as marks of 4-7-1 in foursomes and 5-6-0 in four ball suggest.
In golf's version of speed dating, Woods has been set up with just about everyone but has yet to find someone he truly clicks with.
At Oakland Hills in Michigan in 2004, captain Hal Sutton played the ultimate hunch matching Woods with long-time rival Phil Mickelson in a partnership that failed miserably.
More recently, Woods has seen duty with the ever steady and unflappable Jim Furyk and found some success with the quiet and humble Steve Stricker, one of the best putters on the PGA Tour.
This time it will be up to captain Davis Love III, who has partnered Woods as a player, to find the perfect match for the world number two.
"Tiger can play great and his partner not play well, or the other team play extremely well," said Love. "Somebody has to play in Tiger's bubble and I think that's the challenge.
"Steve Stricker has found his way into that pairing because he can handle everything that's going on around Tiger.
"It's easier to play with Dustin (Johnson) probably or it's easier to play with Jim Furyk than it is to pair a guy with Tiger because you get the extra attention and the extra pressure."