Pennant set to end stint with Stags, eyes return to England or Europe
He arrived at the start of the year as the biggest name to ever play in the Great Eastern-Yeo's S.League and immediately had to get familiar with the likes of Geylang International and Balestier Khalsa.
In a couple of months, however, Jermaine Pennant could find himself locking horns with famous clubs like Newcastle United, Aston Villa and Blackburn Rovers once more.
Pennant's season-long spell with Tampines Rovers will come to an end with a final outing in tomorrow's RHB Singapore Cup final against Albirex Niigata, after he confirmed he will not be signing a new contract for 2017.
With Tampines set to make changes that will ensure their long-term sustainability, the former Arsenal and Liverpool winger is likely to be just one of many big names that will be at a new home next season.
Asked by The New Paper if he could reveal where that possibly could be, he said: "Probably in the Championship back home in England.
"I can't really say (where) because I don't want to jinx anything.
"There's probably an offer in Europe as well, so it'll be one or the other."
While the 33-year-old may already be making plans for the future, he revealed he will look back fondly at his time in Singapore when it eventually comes to an end.
Pennant added: "I've enjoyed playing at Tampines… They've been a great bunch of lads and we're all close like a family.
"We came in second (in the league), one point behind Albirex, we're in the Singapore Cup final and we reached the quarter-finals of the AFC Cup, so, all in all, I think it's been a good season.
"Until we win on Saturday, I won't say it's been a success. It's just sad we can't build on what we've done this year, bring in a few new faces and be even better next season.
"Then, we might have had a team that could win the league and get as far as we can in the AFC Cup, maybe even reach the final."
Tampines chairman Krishna Ramachandra explained that, while he would have liked to keep Pennant, he had expected that they would not be able to satisfy a player of his quality.
"We've been speaking to him in the past few weeks, just like we have been talking to all the players about the future and the type of contracts that would be able to be offered to them," Krishna told TNP.
"The aim was to offer every current player a contract and make sure the budget was not lopsided by awarding any particular player a huge deal in contrast to the rest.
"At the end of the day, this is a team game."
Despite the situation, Pennant maintained a cheerful front when speaking to the media after training at Jalan Besar yesterday evening.
Asked if he understood where the club were coming from, he said: "I'm not quite sure about this whole jackpot thing but I guess that's where a lot of teams get a lot of money from.
"The club want to take a different approach and have made the decision to opt out of this.
"Obviously, taking that stance, cuts have been made and here we are today with a lot of players probably leaving."