Liverpool's January business over recent years has been fairly special, as they've been able to secure players who have become key players, and successes.
The likes of Luis Diaz, Cody Gakpo and Virgil van Dijk have all arrived in the mid-season window and have been great additions, but it hasn't always gone that way. In fact, there have been plenty of misfires that have left the Reds feeling rather blue.
Over the years we've seen Liverpool register some poor January signings and since there isn't a lot of activity expected in the current window, we've decided to look back at the 11 worst January signings the club has made, how many of these do you remember?
1. 11. Takumi Minamino
In terms of the rest of the list, Minamino is far from a flop. Especially considering Liverpool made a profit on his sale to Monaco. Currently, he is tearing it up in Ligue 1 but he failed to break past being a bit-part player at Liverpool despite starring at RB Salzburg prior to joining. Harsh to call him a flop, but he failed to really set the world alight. Photo: Andrew Powell
2. 10. Maurico Pelligrino
Pelligrino was a three-time La Liga champion and there were big things expected when Rafa Benitez brought him to the club. However, he struggled on his debut and made just 13 appearances in total.
3. 9. Fernando Morientes
Arriving from Spain (Real Madrid) with a big reputation, he failed to inspire with just 12 goals in 61 games. A star in Europe but England proved too much.
4. 8. Rigobert Song
Song joined Gerard Houllier's Liverpool in 1999 from Salernitana but failed to make an impact before being phased out. One of the more forgettable signings.