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Roy Jones Jr. left opponent beat up and penniless after brutal ‘winner takes all’ match

Roy Jones Jr.’s career has seen both legendary fights, and bizarre encounters, from fighting a police officer to knocking out a fan, Jones has taken part in some strange matches in his time.

In 1999, Roy Jones stopped police officer-turned-boxer Richard Frazier. In 2016, Jones offered $100K to a fan if they could beat him, leading him to stop debutant Vyron Phillips.

In 2023, he had an unsuccessful comeback against MMA star Anthony Pettis.

These are just some examples of Jones’ more unconventional fights, but there was one, in 2013, which saw Jones, at the age of 44, take on one risky fight.

Roy Jones Jr vs Bernard Hopkins
Photo by Focus on Sport/Getty Images

Roy Jones Jr. fought Zine Benmakhlouf in a ‘winner takes all’ match in Russia

Despite getting on in age and needing to secure as much as he could in what time he had left in the sport, Jones, who played pro basketball before a fight once, risked a fight with 17-3-1 Zine Benmakhlouf on the basis that the loser walks away with nothing.

Roy Jones Jr. in ring with James Toney
Photo by Focus on Sport/Getty Images

Benmakhlouf had lost three times before, with one loss coming to Carlos Takam in his pro debut. Jones, who beat Vinny Pazienza, had lost eight times at this point with a record of 56-8.

The fight did go the distance, but Jones dropped Benmakhlouf with a left hook in the third round, before cruising to an easy unanimous decision victory.

The beating he put on his opponent meant he not only secured the win, but took home all of the purse.

Roy Jones Jr. was knocked out five times in his 76-fight career

Jones Jr., who thinks Jake Paul can become world champ, ended his career with a record of 66-10, but of those 10 losses, only five came by stoppage. This is every stoppage loss Jones suffered in his career:

2004 – Antonio Tarver – TKO2

2004 – Glen Johnson – KO9

2009 – Danny Green – TKO1

2011 – Denis Lebedev – KO10

2015 – Enzo Maccarinelli – KO4