From becoming the Masters' youngest ever champion at the age of 21 to winning the 2008 US Open on one leg, the 49-year-old is not short of happy memories on the golf course.
But Woods may not reflect quite so fondly on his latest TGL outing on Tuesday night, which left the sporting icon slightly red-faced.
Competing for the Jupiter Links in the partially-virtual indoor league, Woods left himself 199 yards to the hole on the 13th after his tee shot.
However, a mix-up followed, as the 15-time major winner heard his teammates say he had 99 yards to go, with players often dropping the first number of the distance when it appears obvious.
Unfortunately this wasn't the case for Woods, who then chose a wedge to hit his next shot 99 yards - leaving him 100 yards short.
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The American was left baffled as his shot fell well short of the green, and immediately sought out his teammates for answers, only to find Kevin Kisner and Tom Kim on the floor laughing.
Footage shows a bemused Woods cry: "No, I heard you say 99! Not 199!" while Kisner and Kim can be seen in stitches.
Explaining the misunderstanding to an interviewer as he approached his team, Woods went on: "I heard 99 yards. So I grabbed my 56 (wedge) and I hit it 100 yards!"
And it appears the humiliation for Woods had not worn off after the close of play, as he later named it among his greatest embarrassments as a golfer.
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Speaking to ESPN afterwards, he said: "One of the most embarrassing moments in my golfing career just happened.
"I just screwed up. That was embarrassing."
Worse still for Woods, the mix-up came as Jupiter Links were beaten 10-3 by New York Golf Club in the event.
And his misfortune drew plenty of reaction online, with his admission prompting golfers online to reflect on their own biggest humiliations on the course.
Taking to X, one fan quickly managed to outdo Woods, as they admitted to falling much shorter than the sporting great.
They simply wrote: "Yardage was 199 and I hit it 9."
Meanwhile, another shared their tale of destruction: "Anytime I hit in front of the clubhouse on 18, I snap-hooked a 4-iron into the parking lot and broke a BMW's window.
"It led to me getting rid of that club shortly after."
Elsewhere, one golfer admitted: "In a US Open qualifier, I played to the wrong green on a hole (to be fair, I had never played the course until that day)
Woods' appearance in the TGL event was his first since he announced the death of his mother, Kultida, on 4 February.
He was accompanied by his 16-year-old son, Charlie, as he walked out for Tuesday's event at the SoFi Center in California, where his late mother had watched him play for the last time on 27 January.