Daniel Agger – 2006 (Brondby)
Agger joined Liverpool on a four-and-a-half-year contract in January of 2006 for a £6 million fee. The left-footed Danish defender began to solidify his spot in the starting XI during the 2006-07 campaign, including an absolute belter from over thirty yards out against West Ham for his first goal in red, and the future was looking bright for Agger.
Unfortunately, from about 2007 onward he was plagued by injury after injury, missing a high number of games each season and ruining his opportunity to have an even more successful career with Liverpool. He left the Reds after 232 appearances across eight seasons, collecting 14 goals, 11 assists, and a League Cup trophy with the club. Agger returned to Brondby in 2014 and retired two years later at the age of 31.
Jan Kromkamp – 2006 (swap, Villarreal)
The Dutch defender joined Liverpool as part of a swap for then-Red right full-back Josemi. Kromkamp appeared in 18 games for the Reds across all competitions, making it into the starting XI 12 times but did not make any sort of impression. Just seven months after arriving in Merseyside, Kromkamp returned home to the Netherlands.
David Martin – 2006 (free transfer, Milton Keyes Dons)
After arriving on a free transfer from Milton Keyes Dons, Martin was repeatedly loaned out by Liverpool until he was transferred back to MK Dons in 2010, having never taken the pitch for the Reds’ first-team.
In 2019, Martin joined West Ham United, where he appeared five times in the 2019-20 campaign including two clean sheets.