When long-haired teenager Andre Agassi made his Wimbledon debut in 1987 he won just five games in his first round defeat by Henri Leconte and could barely disguise his contempt for the All England Club traditions.
Now, nearly two decades on, another bandana-wearing upstart, Spain's Rafael Nadal threatens to bring down the final curtain on Agassi's magical relationship with the grasscourt grand slam that he eventually grew to love.
Nadal, 20, has already written his name in the record books with two French Open victories and 60 consecutive claycourt wins, but Saturday's third round meeting with 1992 champion Agassi will cast him very much as the master's apprentice.
The Mallorcan spin king looked like a grasscourt novice during his five-set victory over American qualifier Robert Kendrick on Thursday, although his ferocious will to win allowed him to recover from a two-set deficit.
The 36-year-old Agassi's back may be creaking these days, but there is very little the American does not know about the subtleties of Wimbledon's lawns.
Nadal was not even born when Agassi played his first professional match. Yet despite his naivety on grass, Agassi knows he will need all his experience to fight off the raging bull on Saturday.
"(Nadal) will have his hands full trying to master grass, no question," Agassi said this week,
"This surface takes an edge off what's happening with his ball...it's more difficult for him to hit it how he normally does. On paper it's not ideal for him.
"But we've seen the way he competes. We've seen what I never thought would be broken in all those matches on clay, the kind of strength that takes mentally and in your heart, it's incredible. If there's somebody that can do it, it can be him."
On slow claycourts Nadal is virtually impossible to pass while on bouncy hardcourts his opponents need step ladders to return his kicking horse forehand.
On Wimbledon's skiddy grass, however, his topspin is muffled and a well placed 125mph serve leaves even him swishing at thin air.
Agassi lost their only previous meeting in Montreal last year, but this time feels the surface will favour him.
"In Montreal, it was a very fast, high bouncing court, you know. His ball was just ugly," he said.
"Here the ball doesn't bounce as high which hopefully will allow me to set a little bit more my ground strokes.
"But, listen, he's very confident a great competitor, very talented and fit. So it's gonna be a hard match."
It should be a fascinating contest and one which three-times former Wimbledon champion John McEnroe is relishing.
"I know that all of us are looking forward to Andre playing Nadal," McEnroe, NBC's lead tennis analyst, said.
"If Agassi is up to it physically, he has the tools, comfort level and type of game to do well on this surface even though he's not a big server or volleyer.
"I think it's a boost for tennis to have one of the all-time greats up against an up and coming superstar. That's the type of match we need."
Nadal plays down his chances, saying he still needs three or four years to have a chance of emulating Manuel Santana, the last Spaniard to win Wimbledon in 1966.
If he beats Agassi and gets into the second week, however, there is no telling how far this extraordinary fighter might go.