1975 was a watershed year for Tampines, as they were promoted to Division I after winning all their league matches and reached the President's Cup final, where they lost 0–1 to the Singapore Armed Forces Sports Association in front of a national record crowd of 30,000.

In 2002, the Stags secured the services of Malaysian coach, Chow Kwai Lam,[2] who guided them to the Singapore Cup and two fourth-place finishes.

[3] The 2000s marked the golden era of Tampines Rovers under Thai head coach Vorawan Chitavanich, during which the club amassed a squad filled with stalwarts like Nazri Nasir, Noh Alam Shah, Sead Muratović, and Rezal Hassan.

On 19 January 2016, Former Arsenal and Liverpool winger, Jermaine Pennant signed a one-year contract which he took a 70% pay cut from his salary earned at Wigan Athletic.

It was reported that he would earn a salary of SGD$40,000 (£19,500) per month, which made him the highest-paid player in the history of the domestic professional football league.

In February, Tampines Rovers started with the 2016 AFC Cup being drawn in Group E with Ceres from Philippines, Selangor F.A from Malaysia and Sheikh Jamal Dhanmondi from Bangladesh.

The Round of 16 was won with 10 men by Tampines Rovers versus Mohun Bagan from India by a late goal from Afiq Yunos in the after extra time which resulted in 1–2 win at the Indira Gandhi Athletic Stadium.

On 14 September 2016, Tampines Rovers continued their 2016 AFC Cup Quarter-finals facing Bengaluru FC from India but was knocked out on a narrow 1-0 aggregate score on a 2 leg basis.

The 3 foreign imports from last season, Billy Mehmet, Jordan Webb and Jermaine Pennant had been released from the club with them joining DPMM, Warriors and Bury respectively.

They would include former Ceres utility player, Son Yong Chan, Japanese teenager winger, Ryutaro Megumi and former Croatia U17 International, Ivan Jakov Džoni.

Notable local signings would include Singapore National Team Defensive Pairing, Madhu Mohana and Daniel Bennett from Warriors FC and Geylang International.

Notable players such as Hafiz Abu Sujad, Afiq Yunos and Fazrul Nawaz had moved to Hougang United.

After coming back from Thailand, they took on NFL Side, Katong FC before facing Johor Darul Ta'zim II and Albirex Niigata (S).

They would kick start their campaign in the 2019 Singapore Premier League season on 3 March 2019 against Hougang United at the Jalan Besar Stadium.

At the same time top striker, Khairul Amri had left to sign for FELDA United in the Malaysia Super League.

This meant that Tampines Rovers would play in the 2020 AFC Cup instead ending up in Group H of the competition with Kaya–Iloilo, PSM Makassar and Shan United.

The Stags goes on to start the league magnificently, winning 3 out of their 3 opening fixtures without conceding a goal and scoring 7 along the way, putting 4 past recently acquired Lion City Sailors.

Competition rule changes included the provision for two water breaks during a match, and clubs will be able to use up to five substitutions (in defined windows after half-time).

While it was a tough debut for Gavin Lee's charges, veteran defender Daniel Bennett did create a slice of history when he scored their only goal during their fifth group encounter against Gamba Osaka in an 8–1 defeat at the Bunyodkor Stadium in Tashkent, Uzbekistan.

The 2021 Singapore Premier League season ended with Tampines Rovers finishing in 4th place which will see them qualified for the 2022 AFC Cup.

The lengthy deal would see Kyoga remaining as a Stag till December 2026 and could also pave the way for another naturalized footballer and also being a Singaporean citizenship.

Tampines Rovers also announced a five-year contract for promising star, Shah Shahiran and Joel Chew committing their future to the club.

Tampines Rovers than replace the last foreigner slot bringing in Miloš Zlatković, Lion City Sailors stars, Faris Ramli and Saifullah Akbar also joined the club.

The Stags see themselves as host of the 2023–24 AFC Cup qualifying ASEAN play-offs zone against Cambodian side, Phnom Penh Crown at the Jalan Besar Stadium on 23 August 2023.

On 22 September in the away fixture against DPMM, Boris Kopitović overtake Aleksandar Đurić to become Tampines Rovers all-time leading goalscorer in the club history.

On 27 November, Seia Kunori scored the only goal in the match to end Bangkok United winning streak in the group stage at home.

On the final day fixtures against Lee Man at the Mong Kok Stadium desperately needing a win, Tampines Rovers felled to a goalless draw which sees the team finishing in third place in the group thus missing out on qualifying to the round of 16.

TYK was formed by a small group of passionate fans with the shared goal of improving the match-day atmosphere at games.

[14] The general Tampines Rover's fanbase has been collectively referred to as “The Stand”[15] – the name likely derived from its similarity to “The Stags”.

Bangkok Glass [2023 Singapore Cup matches only] Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.