Singapore Premier League Awards Night is a football awards ceremony held by the Football Association of Singapore since the S.League's inaugural season in 1996.
Note nationality of players at presentation of award. A number of foreign players were naturalised to play for Singapore later in their career.
^ Goals in all domestic competitions, including the S.League and Singapore Cup.
Source:Web site: S.League leading scorers. S.League.
| 2018 | Zulfadhmi Suzliman | Zulfadhmi Suzliman | Albirex Niigata (S) (20 May 2018) | |
| 2021 | Gabriel Quak | Lion City Sailors | Balestier Khalsa (18 April 2021) | |
| 2022 | Ilhan Fandi |  Albirex Niigata (S) | Balestier Khalsa (16 July 2022) | |
| 2023 | Khairul Amri | Tanjong Pagar United | Hougang United (6 April 2023) |
| Season | Name | Club | |
|---|---|---|---|
| 2005 | Mirko Grabovac | Tampines Rovers | |
| 2007 | Aleksandar Đurić | Singapore Armed Forces |
| Season | Name | Club | |
|---|---|---|---|
| 1996 | P N Sivaji | Tanjong Pagar United | |
| 1997 | Chris Chan | Singapore Armed Forces | |
| 1998 | Alan Wong | Gombak United | |
| 1999 | Kok Wai Leong | Singapore Armed Forces | |
| 2000 | John Yap | Gombak United | |
| 2001 | Noordin Abdul Rahman | Home United | |
| 2002 | Alfred Loi | Sembawang Rangers |
| Season | width='160' | Name! | width='160' | Club | |
|---|---|---|---|---|---|
| 2002 | align='left' |  Sead Muratović | align='left' | Tampines Rovers | |
| 2003 | align='left' | Indra Sahdan Daud | align='left' | Home United | |
| 2004 | align='left' | Agu Casmir | align='left' | Young Lions | |
| 2005 | align='left' | Zulkarnaen Zainal | align='left' | Tampines Rovers | |
| 2006 | align='left' | Khairul Amri | align='left' | Young Lions | |
| 2007 | align='left' | Aleksandar Đurić | align='left' | Singapore Armed Forces | |
| 2008 | align='left' |  Kengne Ludovick | align='left' | Home United | |
| 2009 | align='left' |  Gabriel Obatola | align='left' | Gombak United | |
| 2010 | align='left' | Shahril Jantan | align='left' | Singapore Armed Forces | |
| 2011 | align='left' | Safuwan Baharudin | align='left' | Young Lions | |
| 2012 | align='left' |  Wan Zack Haikal | align='left' | Harimau Muda A | |
| 2013 | align='left' |  Mamadou M. Diallo | align='left' | Hougang United |
The Dollah Kassim Award is an annual award handed to the most outstanding youth player aged 18 and below. The winner will receive the Singapore Pools' Passport to Excellence prize which funds the cost of sending the recipient for an overseas training stint. Singapore Pools launched the incentive in 2010 to nurture young sports talent recognising footballing excellence and character.
| 2010 | Ammirul Emmran | Newcastle United | |
| 2011 | Adam Swandi | Newcastle United, Chelsea and Atlético Madrid. | |
| 2012 | R. Aaravin | FC Metz | |
| 2013 | Hazim Faiz | ||
| 2014 | Muhelmy Suhaimi | ||
| 2015 | Joshua Pereira | Saint-Étienne | |
| 2016 | Rusyaidi Salime | Omiya Ardija | |
| 2017 | Joel Chew | ||
| 2018 | Nur Adam Abdullah | KRC Genk | |
| 2019 | Iman Hakim | Omiya Ardija |
