Liverpool shattered its club record to secure Alexander Isak on transfer deadline day after witnessing the Sweden international help engineer his departure from Newcastle United. However, throughout the summer, the Magpies had remained resolute that the striker was not available for purchase.
At one stage, it appeared the Reds might have been forced to bide their time in their pursuit of the 25 year old, only for Newcastle to relax its public position as the transfer window drew to a close.
As a result, Liverpool succeeded in its bid to acquire Isak. Yet before the Reds finalised their deal for the striker, supporters were reminded of the club's previous record acquisition of Virgil van Dijk.
The Dutchman arrived at Liverpool in a £75m transfer from Southampton in January 2018. However, his switch only materialised after the Reds had been compelled to abandon their pursuit of the centre-back the preceding summer following accusations of making an unauthorised approach to Van Dijk.
In an official statement at the time, the club said: "Liverpool Football Club would like to put on record our regret over recent media speculation regarding Southampton Football Club and player transfers between the two clubs.", reports the Liverpool Echo.
"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."
That did not prevent Liverpool from renewing their pursuit the subsequent window and securing Van Dijk in a £75m agreement. Reflecting on the transfer saga, former Southampton CEO Martin Semmens has now confessed that he finds the way the Saints handled the situation at the time 'embarrassing'.
He revealed how Liverpool's behaviour had irked Southampton, and also admitted that forcing Van Dijk to remain at St. Mary's backfired on the club.
"Virgil van Dijk was a big one for us," he reminisced on TalkSPORT. "We treated him in a different way and said, 'You can't go'. It didn't work well for us.
"We didn't [get him back on our side]. Virgil was fantastic, in my opinion, he trained at 75 [percent] and played at 75 [percent] and was still the best player in the team, if not the league.
"He didn't cause us any problems. He never said a single bad word to anyone, but he wanted to go, and it wasn't effective for us to keep the player.
"We kept him until January. It wasn't good for the squad or the environment, but to be clear, Virgil never said one negative word to anybody.
"We felt, at the time, we could get more if he stayed. He'd had a bad injury, I think he'd been out for six to nine months and we felt that he owed us, which is embarrassing now I think back to it.
"There was also some contact from Liverpool we didn't love. At that time, probably a little more for the morals, he had already met Klopp before he told us.
"But in the end, he did a very good job for us and we sold him for a good price."