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The Liverpool fan now has a bout at Anfield in his sights.
Pimblett moved into the top-10 of the UFC lightweight division after the triumph over highly-ranked Chandler at the Kaseya Center - with the 30-year-old Scouser making known his desire to fight a top-five opponent in his next bout, with his eyes then on a title tilt.
Instead, McGregor was reported to have lost $500,000 by backing the defeated American.
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Pimblett, who has long stated his desire to fight at Anfield - the home of his beloved Reds - was quizzed about McGregor's bet, telling TNT Sports: "I thought you would have backed your own.
You could do that at Wembley.
"Me and Conor sells Wembley out, sells Anfield out, sells Croke Park out.
Anyone."
Pimblett has been vocal in the past about his wish to fight at Anfield, telling Sky Sports the week before the bout with Chandler that he'd even gone as far as inviting UFC staff to come to Liverpool's home stadium, to experience the atmosphere for themselves to sell the idea to them.
He added: "I've always said my dream is to fight at Anfield.
They don't like doing stadiums, especially in the UK [due to weather], but I don't dream of fighting anywhere else but Anfield."
Liverpool have turned Anfield events in the summer as something of a spectacle.
The Swift concerts earned more than £10million in revenue for the club last year, and a fight of the magnitude of Pimblett and McGregor would likely carry a significant value for the club, who are paid by promoters for the rental of the stadium as the bulk of income.
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McGregor's odds of stepping out of his unofficial retirement don't seem promising, however, with the 36-year-old having pulled out of what was supposed to be his comeback fight in June of 2024 at UFC 303, ironically against Chandler and showing little sign of a return to the Octagon after taking time away from the sport at his residence in Dubai.
But Pimblett could still land his dream venue if he continues his ascent, and his win at the weekend has put him in a strong position to make his dream a reality.