Raheem Sterling was booed when collecting his award for Liverpool's Young Player of the Year amid uncertainty over his future.
Sources have told ESPN FC that Sterling, 20, is set to tell Liverpool he wants to leave the club in the summer when talks between the two parties resume this week.
The England international is under contract at Anfield until 2017 but the club and player have so far failed to agree on new terms, with Sterling having turned down £100,000 a week.
Last month, Sterling was heckled by a fan at the launch of the club's new home kit over his decision to reject a new contract offer.
On Tuesday night, Brendan Rodgers' squad attended their season awards ceremony, with Sterling among the players in attendance.
The winger, who has scored seven Premier League goals this season, was named Young Player of the Year but was, according to journalists in attendance, booed by some of those at the event.
Raheem Sterling wins #LFC young player of the year. Fans shout 'are you staying?' He's then booed by some as he leaves stage
- Ben Smith (@BenSmithBBC) May 19, 2015
As Sterling made a short acceptance speech there were shouts of "Stay Raheem" and as he finished speaking and left the stage there were audible boos from some of the 3,000 fans assembled at the rear of the Echo Arena in the city.
When his name was mentioned in a video montage moments later there were more jeers.
Philippe Coutinho was also rewarded for his performances this season, with the Brazilian named first-team Player of the Year and given Performance of the Year.
Manager Rodgers, presenting the goal of the season award to Coutinho for his strike against Southampton, believes his side will be better for their difficulties on the pitch.
"Expectancy from last season was going to be high [after finishing second]. Things that have happened, the distractions, you can't plan for them," he said.
"It has been a difficult, trying season but the players will all be better for it next year.
"The players need a rest [but] the club will continue to work hard to improve the squad and next year provides another great opportunity for us like last season."
Information from the Press Association was used in this report.