Liverpool have tended to avoid doing their business in the winter window, although when Jurgen Klopp spots an opportunity to improve their squad, they seize it – Gakpo is the latest example.
The Reds have spent the bulk of their transfer fees in the summer window, although there have been some exceptions in the last seven years.
We've ranked his seven January signings at Liverpool by Jurgen Klopp from worst to best.
7. Ben Davies:
After suffering an injury crisis in defence, Liverpool made a surprise move to sign Davies from Preston North End in January 2021.
But he didn't make a single first-team appearance in the second half of 2020-21, with Klopp preferring to play midfielders Jordan Henderson and Fabinho in defence.
The centre-back fell further down the pecking order following Ibrahima Konate's arrival and joined Championship side Sheffield United on a season-long loan deal last term.
"I was becoming aware that I was the fifth or sixth choice to play in the centre of the defence for Liverpool," Davies told The Daily Mirror in September 2021.
"When I joined Sheffield United, with the promise of playing games, it felt like I had finally been mentally released."
Davies never made an appearance for Klopp's Reds. He joined Rangers on a permanent deal in the summer, and Liverpool actually made a small profit.
6. Steven Caulker
Despite playing in Southampton's 6-1 defeat to Liverpool in December 2015, Caulker seemingly did enough to impress Jurgen Klopp and joined them on loan a few weeks later.
If that wasn't strange enough, the center-back was used as an emergency striker during his three Premier League appearances for the club.
"I was shocked, I thought the gaffer was joking when he said it (go up front)," Caulker said after making his debut in a 3-3 draw with Arsenal.
He failed to find the back of the net but his presence in the penalty area did lead to Adam Lallana's late winner against Norwich City.
Caulker returned to defence for an FA Cup tie against West Ham before spending the remainder of his loan spell with Liverpool's Under-23s.
5. Ozan Kabak
After Joel Matip suffered an injury two days before the January transfer deadline in 2021, Liverpool reacted by signing Kabak from Schalke on a six-month loan deal.
The defender had a calamitous debut for the Reds as he collided with Alisson Becker and gifted Leicester's Jamie Vardy the easiest goal of his career.
He recovered from that rocky start and made another 12 appearances for Klopp's side, helping them finish third in the Premier League and reach the quarter-finals of the Champions League.
But Liverpool still decided against spending £18million to sign Kabak on a permanent deal and then brought in Konate from RB Leipzig.
4. Marko Grujic
Grujic became Klopp's first signing as Liverpool manager in January 2016, joining the Reds in a £5.1million deal from Red Star Belgrade.
The midfielder was regarded as a highly-rated prospect but made just 16 competitive appearances for Liverpool's first team, scoring his only goal for the club in a 7-2 win over Lincoln in September 2020.
He spent time out on loan at Cardiff City, Hertha Berlin and Porto before being sold to the latter in a £10.5million deal in 2021.
Not bad business for a player they had absolutely no intention of using.
3. Takumi Minamino
After impressing for Red Bull Salzburg against Liverpool in the Champions League group stages, Klopp bought Minamino for just £7.25million in January 2020.
He has unsurprisingly struggled to break up that front three, starting just four Premier League games in 2020 before spending time on loan at Southampton.
The Japan international returned to Anfield and played a useful role as a squad player as Liverpool chased the quadruple last term, particularly in the two domestic cups, but he ultimately failed to nail down a first-team role.
Minamino departed in the summer, joining Monaco for a fee in the region of £13million. Another profit made.
2. Luis Diaz
The Colombia international gave Liverpool a shot in the arm midway through the 2021-22 campaign, hitting the ground running immediately and proving an inspired addition as they competed on four fronts.
Diaz has struggled to have quite the same impact in his first full season at Anfield, which has been plagued by injuries, but he looks set to be a vitally important player for Jurgen Klopp in the years to come.
1. Virgil van Dijk
There was only ever going to be one winner…
After failing to sign Van Dijk from Southampton in the summer of 2017, Liverpool refused to be deterred and met the £75million asking price in January 2018.
The Netherlands international had a transformative effect on the Anfield backline and proved to be the final piece in the puzzle for Klopp, while his season-long absence in 2019-20 demonstrated quite how important he is.
He won the PFA Player of the Year award and the Champions League in his first full season at Liverpool before lifting the Premier League title in 2020, going on to complete the set with the FA Cup and League Cup last term.
"Virgil's arrival was obviously a big day in our common history and is a good example for a winter transfer how it works," Jurgen Klopp said in 2021. "I think a winter transfer works when you wanted to sign the player either the summer before or the summer after anyway.
"That was the situation, we wanted Virgil in the summer already, for some reasons we couldn't do the transfer, but then in the winter we tried again and could get it through.
"It was a very important day and changed a lot for us because in combination then with Joel