From the heady heights of the Champions League final and the big English Premier League games, the career of Jermaine Pennant, at one point the most expensive teenager in British football, might not have gone as planned.
Tonight, he will lace up his boots in a more humble setting of the Asian Football Confederation (AFC) Cup, as his Tampines Rovers tale on Selangor in Asia's second-tier club competition.
Yet, while the occasion is far from the grandest he has performed in, today's match against Selangor - at the 55,000-seat National Stadium - will be his most important since his foray into South-east Asia.
Only a win will do for the Stags who, entering the final match of the group stage, are third in Group E with seven points, one behind their Causeway rivals and two behind leaders Ceres of the Philippines.
Only the top two teams qualify for the round of 16, and Pennant, 33, had no qualms accepting that the onus is on him to carry the Stags to the next stage.
ARENA FIT FOR STAR PLAYER
It's better to play in a stadium like this. It feels more like playing in Europe. In all fairness it's easier for me to play here.
JERMAINE PENNANT , on playing at the 55,000-seater National Stadium.
Asked if this is the time for him to justify the hype that surrounded his signing, Pennant told The Straits Times without hesitation: "I thought I've stepped up since I've been here. You've got to deliver in games and every game I've played in, I have delivered.
"Against Warriors (on Apr 30) we were losing 2-1 until I came on at half-time and we won 4-2. To me that's delivering."
Still, expectations on him and the team are high. After all, this is the first time an S-League club will be playing at the National Stadium since it reopened its doors in 2014.
Tampines' big pre-season moves, in which they also signed eight members of the now-disbanded LionsXII, means that progress to the AFC Cup knockout stage is not so much a target as it is a prerequisite.
But the pressure is something Pennant, one of Liverpool's standout performers in their 2007 Champions League final defeat by AC Milan, relishes.
The winger, who has three league goals to his name so far, said: "It's better to play in a stadium like this. It feels more like playing in Europe. In all fairness it's easier for me to play here. I'm confident. I've prepared well all week and honestly I can't wait for the game to start."
While the spotlight will be on him, Tampines' leaky defence - an irony considering coach V. Sundramoorthy's lauded defensive nous - will need to hold up, especially since Selangor coach Zainal Abidin Hassan has signalled his intentions to attack.
Tampines boast the dependable Izwan Mahbud in goal but lapses in concentration had seen the Stags concede three penalties in their last two AFC Cup games.
Sundram said: "We've been making mistakes in defensive areas, that's our main problem. We need to stay focused. But if the boys are willing to fight and run for everything, and play to our game-plan, then we can get a win."
In the reverse fixture at the Selayang Stadium, where Pennant did not feature, Tampines won 1-0, and Sundram said this will give his team a psychological advantage.
On his star man, the coach said: "For Jermaine, (handling the occasion) will be a piece of cake.
"I can see that he has the desire to go out there and entertain the crowd and at the same time do well for the team.
"Now he's fully fit, ready and eager to go. That's very important for us."
TAMPINES V SELANGOR
StarHub Ch210, 6.50pm