The former Arsenal and Liverpool star reportedly racked up debts of more than £1 million (S$1.62 million).
Daily Mail reported that the former Premier League star owes money to creditors including HMRC (the British equivalent of our IRAS), councils, banks and utility companies.
The former midfielder is understood to have defaulted on his mortgage payments, Daily Mail further reported.
He was given a one-year bankruptcy order at Birmingham county court, The Sun added.
According to The Sun, a source close to Pennant said: "His debts are into seven-figures."
"His debts to the taxman and banks are huge."
"He has defaulted on mortgage payments and will likely have property repossessed.”
Creditors took Pennant to court after he failed to settle a number of outstanding bills, The Sun also reported.
Pennant's media company, Jermaine Pennant Ltd, was dissolved in 2020.
He had set up the company to handle his pay from "Celebrity Big Brother" and screen appearances.
According to Daily Mail, Pennant's £3 million property, which was bought in 2006, stood empty from 2020 following his split from then-partner Alice Goodwin.
Pennant came to Singapore and joined Tampines Rovers at the start of 2016.
He stayed for one season at the club.
His S-League stint lasted nine months.
The former England Under-21 international was believed to have been earning around S$20,000 a month -- big money by S-League standards.
Before he left Tampines Rovers, he was understood to have received offers from UK clubs, as well some Southeast Asian clubs.
Prior to coming to Singapore to play in the domestic league here, Pennant was drawing some £25,000 (S$52,286 then) a week at his last club Wigan Athletic.
Before he signed for Tampines Rovers back then, Pennant was asked about the probability of the deal happening, and he said: “I know it’s not a massive paying league."
"I don’t expect to come here for English wages. I understand there might be a drop but at the same time the club has to appreciate where I am coming from."
"I am not coming here to be greedy, I am coming here to progress my career and maybe help Singapore so I am hopeful that a deal can be agreed."
Pennant's presence did bring some hype to local football back then.
A pre-match friendly against Hougang United at the Jalan Besar Stadium attracted close to 2,000 fans.
He was mobbed.
But the season for Tampines Rovers with Pennant was found wanting.
The five-time S-League champions at that time finished second in the S-League, one point behind Albirex Niigata -- with two games to spare.
Albirex also knocked out Tampines in the League Cup semi-final.
Top photo via Jermaine Pennant & Lim Weixiang