During the 2018 FIFA World Cup qualifiers, Japan was held to a draw at home at the Saitama Stadium by Singapore, being the only game where they had dropped points in the group.

[10] Singapore won the bronze medal in the 1995 Southeast Asian Games,[11] after losing 0–1 in the semi-finals to the hosts and eventual gold medalists, Thailand.

[15][16] However, in the 1998 edition of the AFF Championship, Singapore's team led by coach Barry Whitbread won the group stage with victories over Malaysia and the Philippines.

[18] Jan B. Poulsen, who was part of Denmark's backroom staff at the 1998 FIFA World Cup, was appointed the Technical Director of the Football Association of Singapore in 1999.

In the final against Thailand, Singapore won a controversial first leg at home 2–1, then secured a 1–1 draw in Bangkok thanks to a late strike from Khairul Amri to retain the AFF Championship trophy.

Their second round opponents were regional rivals Malaysia, whom they beat 5–3 in the first leg with goals from Aleksandar Đurić, Qiu Li, Mustafic Fahrudin and Shi Jiayi.

A 1–1 draw thanks to a key Shi Jiayi goal in the second half was enough to put Singapore through to the third round of 2014 FIFA World Cup qualifiers.

In the preliminary draw in Brazil on 30 July 2011 by the football governing body FIFA, Singapore was drawn into Group A for their Round 3 of the Asian qualifiers with Jordan, Iraq and China.

In October 2013, Singapore hosted Syria at the Jalan Besar Stadium and with their first win of the campaign with a 2–1 victory thanks to Gabriel Quak's late winner which was also his first international goal.

LionsXII midfielders Gabriel Quak and Faris Ramli and Tanjong Pagar United's winger Hafiz Nor also received their first national call-ups.

In April 2016, a month after the match against Afghanistan, the FAS announced that Bernd Stange contract would not be renewed and he left the Singapore national football team.

In 2016, Sundram also called up a few uncapped players like Syazwan Buhari, Khairulhin Khalid, Irfan Fandi, Abdil Qaiyyim, Shawal Anuar, Azhar Sairudin and Amy Recha.

Singapore's head coach V. Sundramoorthy introduced a National Team Day where Mondays are for players who are called up for a short meeting and tactical training session in the pitch.

Singapore finished bottom of the group with 2 points, losing the final match 1–0 to secure home-and-away losses against Chinese Taipei on 26 March 2018.

On the reverse fixtures on 25 December 2021, Singapore was in a 2–1 lead after a freekick goal from Shahdan Sulaiman but all hope seems lost where Pratama Arhan ties the deficit for Indonesia which see the match going into extra time.

On 28 December 2021, Yoshida ended his stint as a head coach by mutual agreement citing family reasons after the Singapore team reached the semi-finals.

Nazri Nasri was the interim coach overseeing Singapore's participation in the 2022 FAS Tri-Nations Series consisting of Malaysia and Philippines at the National Stadium.

The first leg took place at the National Stadium, which saw a total number of 10,355 spectators in attendance as Singapore gained the upper hand with a 2–1 victory with goals from Christopher van Huizen and Jacob Mahler.

However, the fans weren’t too satisfied with the performances as Singapore missed a lot of scoring opportunities sorely, lacking the composure in front of goal with the advantages of playing at home.

The team then travelled to Dededo facing Guam in the second leg on 17 October at the GFA National Training Center where Shawal Anuar scored the only goal in the match securing the win.

Singapore then advance to the second round being grouped with Asian powerhouse South Korea, China and Southeast Asia rivals, Thailand.

During the 2026 FIFA World Cup qualification match on 21 March 2024, Singapore played at home to China, where they trailed 2–0 with Wu Lei scoring both goals, before Faris Ramli and Jacob Mahler secured the comeback to upset the visitors and hold them to a 2–2 draw.

Five days later, Singapore ended their World Cup qualification campaign with a 3–1 away loss to Thailand to end their run in bottom, but it was notable as Singapore's valiant performance, notably with goalkeeper Hassan Sunny making 13 saves and Ikhsan Fandi's equaliser, proved to have made the difference as Thailand's victory was not enough to seize the second place from China, which progressed via superior head-to-head record.

The kit was worn for the first time by the national team in the international friendly against Australia in preparation for the 2010 FIFA World Cup qualifier home game against Lebanon on 26 March 2008.

Since 2023, the numbers of home attendance rise up where it sold 29,644 tickets during the 2026 FIFA World Cup qualification (AFC) match against Thailand in November.

When football fever for these two national teams was at its peak in the 1980s and early 1990s, queueing overnight for tickets was not uncommon where the rivalry lays dormant for a number of years.

After Singapore advanced to the third round of 2010 FIFA World Cup qualification, at the expense of Malaysia, beating them 6-4 on aggregate, an online war broke out among its supporters.

Malaysian fans, incensed by what they felt was the Lions' time-wasting tactics during the second leg of the second-round qualifier in Kuala Lumpur, created a Facebook page mocking the Singapore national side.

Tensions ran high during the first leg in Singapore on 23 July 2011, when missiles from Malaysia's travelling fans rained down on the Jalan Besar Stadium field after the Lions' fourth goal.

Water bottles were aimed at the Singapore players after the final whistle, while Lions goalkeeper, Izwan Mahbud was targeted by laser pointers during the game to distract him.