Wednesday was one of the roughest hump days in recent history for Liverpool Football Club.
Earlier on in the day, it seemed as though they had given up on the appealing signing of Mohamed Salah from Roma as their attention turned to little-known Sporting winger Gelson Martins.
But things got much, much worse.
The red half of Merseyside was forced to release a statement apologising to Southampton for their pursuit of Virgil Van Dijk after the Saints complained to the Premier League about Liverpool's illegal pursuit.
The statement read: "Liverpool would like to put on record our regret over recent media speculation regarding Southampton Football Club and player transfers between the two clubs.
"We apologise to the owner, board of directors and fans of Southampton for any misunderstanding regarding Virgil van Dijk. We respect Southampton's position and can confirm we have ended any interest in the player."
But according to Jeremy Wilson of The Telegraph, Liverpool's apology has done no good and the south coast club have no plans of dropping their complaint.
Wilson goes on to say that the Premier League are unlikely to investigate if the clubs can settle the matter themselves, but the Reds' prompt apology suggests that they knew they were guilty and feared the repercussions.
Furthermore, Jurgen Klopp's men are already serving a two-year transfer ban on academy players after 'tapping up' a 12-year-old from Stoke and one could assume that Liverpool may have faced a lengthy ban if they were sanctioned again.
While their chances of signing Van Dijk seem to be over, club legend Jamie Carragher is still hoping Liverpool can make some significant signings this summer.
"You never know who the club are going to buy," Carragher said. "But I'm the same as any supporter this season, there's always that hope and optimism that you're going to get all the targets that you want.
"It never really happens but that's the same for any club. I'm sure at times you get number two or three on the list but that's football, and that's the way it goes.
"Hopefully for Jurgen Klopp and Liverpool, they get everyone that they want."
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