Geylang International will become the second Great Eastern Yeo's S.League side to embark on their RHB Singapore Cup journey on Tuesday when they host Lao Police FC at the Bedok Stadium.
The Eagles' sole triumph in Singapore's biggest cup competition came in 2009, when they edged out Thailand outfit Bangkok Glass 1-0 to win the coveted title.
In defender Syed Thaha, they have a player who has tasted success in cup competitions for two successive seasons.
In 2013, he helped Balestier Khalsa to League Cup glory as they memorably smashed Brunei DPMM 4-0 in the final for the club's first-ever local trophy.
The 30-year-old then played an integral part in their triumphant Singapore Cup campaign last year, though he went off with injury during the win against giants Home United in the final.
"Last year's victory with the Tigers was one of my greatest wins even though it was my second time winning the Singapore Cup," Thaha told ESPN FC as he recalled the strong team spirit that aided them. "We pulled through together to put Balestier on the [Singapore football] chart and I am proud of that."
Remarkably, the left-back had also been part of Geylang's winning team in 2009, making him a cup specialist in the Singapore domestic scene.
Thaha, who left Toa Payoh and returned to Bedok before the start of this season, is keen for more success and believes they have what it takes to go all the way again.
"I believe all clubs will have that motivation to push and win the title every year; the same goes for me - I am looking forward to winning," he said.
"I believe we can [go far] as our team spirit has gotten better. We have proved that we are capable of winning matches. I believe in my team and I know we can do well this season."
There are others in this Geylang team with Singapore Cup final experience: goalkeeper Yazid Yasin, midfielders Nor Azli Yusoff and Shah Hirul are all winners, while defenders Hafiz Ozman and Anaz Hadee and winger Hafiz Nor have runners-up medals.
The Eagles' vast experience on the pitch could come in handy against their Laotian opponents, whom they will not take lightly despite being favourites to come out on top.
"We don't know them that well but our coach (Jorg Steinebrunner) says that they are a good team and we can't take it easy," Thaha asserted. "They have very good foreigners and they have also played in the AFC Cup before."
A good start to the Cup will also be a soothing balm after a disappointing league loss to struggling Hougang United last time out.
"We know mistakes were made during that match but that won't stop us from getting better," Thaha said. "We look forward to every game with a winning mindset; every defeat needs a bounce-back, so I hope we can do it."