When Philippe Coutinho handed in a transfer request at Liverpool on the eve of the Premier League campaign, the club must have been thinking ‘oh no, not again’.
In recent years, the Merseysiders have been unable to keep hold of their star players whenever they’ve wanted out with the likes of Fernando Torres, Luis Suarez and Raheem Sterling all agitating moves away from Anfield.
However, this summer was different.
Having qualified for the Champions League, the Reds were able to stave off interest from Barcelona to keep Coutinho at the club.
That wasn’t the case with the aforementioned trio, though.
Torres pushed through a move to Chelsea while Suarez - who was initially denied a move to Barcelona, eventually moved to the Camp Nou in 2014.
But it was the sale of Sterling that was the most disappointing.
Liverpool signed Sterling as a 15-year-old from QPR and helped him develop as a player by giving him plenty of first-team opportunities.
However, five years after joining the club, Sterling wanted to leave despite still only being young.
He refused to travel on the pre-season trip to the Far East and missed training by phoning in sick.
It was something that angered Steven Gerrard who had only just left the club for LA Galaxy himself.
What Gerrard said about Sterling
Looking back on his comments three years later, the former captain didn’t hold back on giving his thoughts on the then 20-year-old.
"I'm not happy with all that carry-on. He needs to go in and see the owners," said Gerrard.
"You don't have to throw in illness, or refuse to go on tour. There are millions of Liverpool fans waiting to see Raheem pull on a Liverpool shirt.
"It looks very disappointing from where I'm sitting. The fans have shown him great support, they want him to stay and I believe that he should too.
"It's very difficult for me to sit here and support him and the team around him - what they're trying to do with his career at a young age.
"It'll be a terrible shame if he goes somewhere and doesn't kick on as a player."
Gerrard compared Sterling to Henderson
In comparison, Gerrard suggested that Sterling take a leaf out of Jordan Henderson's book - who had just inherited his captain’s armband on Merseyside.
"Raheem and Jordan are at different ends of the scale," Gerrard added. "Jordan's so professional, he's a winner, a great lad.
"I don't think there's a more fitting player to take that armband off me. I see a lot of my game in Jordan's game and what I like about him is he's very humble."