Back in 1987, the talented baseliner believed he did not possess the tools to make an impact on the slick surface of the All England Club and duly packed his grasscourt shoes away after a first-round thrashing.
He described the outing as "a short experience, probably an hour and seven minutes on court number two against Henri Leconte and swore I'd never be back".
Sure enough, the Las Vegan showman kept his word and boycotted the event for three years.
"I didn't have any desire to be on the grass, I didn't feel it was tennis," said Agassi.
"I remember feeling it was inconvenient in my schedule. A lot of things that really had nothing to do with the reality of what it was.
"I just didn't have the desire to come over and play on a surface I was convinced that I couldn't really do well on."
At the time, when image meant everything to him, Agassi even blamed his absence on Wimbledon's all-white dress rule and declared he did not own any suitable attire for the championships.
With a penchant for outlandish outfits, Agassi was determined to make a stand but before long his better sense prevailed.
"As I got older then I became aware of what place Wimbledon has in the sport of tennis. To miss out on that was my loss."
Having decided he could live with the strict dress code for two weeks, it did not take long for Agassi to recognise Wimbledon's unique position on the sporting calendar.
To his own astonishment, he landed his first grand slam title on the hallowed turf in 1992 by defeating favourite Goran Ivanisevic in a five-set tussle.
Eleven years on and at the age of 33, the American is preparing his 13th assault on the title and remarkably is second favourite to win it behind defending champion Lleyton Hewitt.
But ask him about his first triumph and he can ramble on endlessly about the finer points of the final as if it was just moments ago.
"I wouldn't say I remember every point...Goran served 38 aces that day, I spent a lot of time walking back and forth between deuce court to the ad court," said Agassi, who lost three grand slam finals before achieving his breakthrough.
"I remember a second serve on set point that caught the chalk up the middle of the ad court, Goran serving 6-5, second serve, thought I was going to get a double there and it dropped in...
"When I got to match point it sort of hit me, I knew I had to make one good shot to become champion.
"I got the chills all through my body and I was telling myself, 'Just hit the ball'.
"I did not want to look back at possibly my only chance ever to win the title and not feel I didn't take my chance. When I won, I still can't really recall much. I was just in shock."
Having discovered the winning formula and now hungry for success, Agassi captured the U.S. Open in 1994 and the Australian Open in 1995.
A mature and more philosophical Agassi finally completed his grand slam journey in 1999 by winning the French Open, becoming only the fifth man to have claimed all four of the major titles.
Not satisfied with increasing his grand slam haul to eight titles by lifting the Australian Open again in January, Agassi this week reclaimed the world number one ranking to become the oldest player to hold the top spot.
"It's tough when you're 16 years old trying to make it in a professional world, you're trying to figure things out and find it challenging but you're tortured by it at the same time," said Agassi, who keeps his trophies in his Las Vegas gym as a reminder of why he continues to push himself to the limit.
"The same thing happens when you're 33, it's just that the challenges are different.
"For me, I still have more to pull out of myself...the desire is still there.
"Some days are easier than others. Those are my challenges as when you've played over a thousand matches, you've seen it all.
"You know how things unfold when certain things happen and you have to find a way to change that and make something better happen for yourself. That gets tougher and tougher and yet it's more rewarding if you can find a way to do that.
"It's like what I experienced this year in Australia. I'd stay on another five years to have one day like that."
With no Pete Sampras or Pat Rafter in the draw, this could well turn out be Agassi's year.
"Wimbledon has it's own magic and it's own rightful place...and it will be incredible to win it again. It feels like it was yesterday yet it feels like a lifetime has happened."