Just three years after leaving his boyhood club Arsenal, the north Londoner would never have thought he'd be sharing the pitch with the greatest ever.
Having joined Coventry from the Gunners' academy in 2000, the Englishman took the then-fairly unprecedented step of plying his trade abroad when he signed for then Serie A side Perugia in 2003.
More incredibly, he found himself locking horns with some of Serie A and football's greatest stars of all time in Ronaldo, Roberto Baggio and even Andrea Pirlo.
Bothroyd managed to get his hands on some iconic shirts during his brief stint in Italy and continues to cherish them to this day.
Who was the best the striker faced? The answer is simple.
"The best defender I played against was [Milan legend] Paolo Maldini," he told talkSPORT.
"Without a doubt, he read the game really well, his distribution was really good, he was always organising the back four.
"You could see the leadership oozing out of him, the way he conducted himself on the pitch."
Bothroyd also revealed what it was like plying his trade abroad, in a league full of star-studded football icons, where nobody hardly anybody spoke English.
"Obviously, there was Fransesco Totti, Alessandro Del Pierro and Kaka, them type of players, they are on the other side, attacking.
"When I went there, I played computer games likes Pro Evolution Soccer [PES] and the first FIFA, and used to use to play as AC Milan.
"I remember it was the third game of the season, and I am lining up and you see the AC Milan team strolling out and I am standing next to Cafu, Paolo Maldini, Gennaro Gattuso and Clarence Seedorf," he recalled in wonder. "I was in awe at that point.
"We played against Siena in the first game, and then Parma in the second match, and I did not really know anyone in the sides.
"Then AC Milan came, and I was like 'wow', it was amazing, I knew virtually all the names."
After his spell came to an end in Italy, he went back to England after Perugia's relegation was confirmed in 2004, joining Blackburn on loan in the 2004/05 season before moving permanently to Charlton in the summer of 2005.
He later got his first and only cap for England while playing for Championship side Cardiff City, but his spell in Italy will no doubt be the long-lasting in his memory.