Hassan Sunny, from S.League champions Warriors FC, made history by becoming the first goalkeeper to win the S.League Player of the Year award since the league's inception in 1996.
The Singapore international custodian has been in outstanding form. Alex Weaver's Warriors stunned Brunei DPMM FC to nick the league title on the final day of the season.
He was up against some strong competition in the shape of Goran Ljubojevic (Balestier Khalsa FC), Rodrigo Tosi (Brunei DPMM), Fazrul Nawaz (Home United FC) and Kazuki Sakamoto (Albirex Niigata Singapore FC).
Hassan's Warriors teammate Nicholas Velez was named Young Player of the Season with his 21 goals helping the club to their first league title since 2009.
The club from the west also went away with the Fan Club of the Year prize to make it a hatrick of wins at the S.League Awards Night, held at Singapore's ITE College East in front of hundreds of fans, players and officials.
Marko Kraljevic walked away with the Coach of the Year award having led Balestier Khalsa FC to their first-ever RHB Singapore Cup on Friday while DPMM FC's Brazilian striker Rodrigo Tosi took home the Top Scorer award.
The biggest night in S.League football was a special one. Qiu Li received an award for hitting the 100-goal mark in the S.League while retiring striker Aleksandar Duric was presented with a special award to commemorate his stellar achievements in Singapore football.
Tampines Rovers' Duric, a former Bosnian refugee who earned 53 caps for his adopted nation, is retiring at the age of 44 after 376 goals during his Singapore career.