Liverpool will host Rangers on Tuesday night in the Champions League, in what will also be the first-ever competitive meeting between the two clubs.
Despite never playing each other before, there have been strong links between the two sides over the years. That was especially the case during Steven Gerrard 's three-and-a-half-year spell in charge at Ibrox.
The Reds legend used his former club to boost his squad on several occasions, leading to a famous Scottish Premiership title win in 2021.
Here, Mirror Football looks at the four Liverpool players who spent time at Rangers during Gerrard's time in charge.
Jon Flanagan
The first of the Liverpool players Gerrard brought to Ibrox was Jon Flanagan, with the full-back a regular in his first season in Scotland. But a hernia injury derailed his second campaign, with the Englishman making just nine appearances before he was released in 2020.
“I thanked him [Gerrard] for giving me the opportunity to spend two years at Ibrox and told him I’d had a great time working with him. There are no hard feelings. At my age, I need to be playing regular football. If I wasn’t going to get that chance at Rangers it makes sense for us to go our separate ways,” he later told The Athletic.
Flanagan would join Belgian side Charleroi, though failed to make an appearance for Les Zèbres. He is now a free agent after a season-long spell at Danish second tier side HB Køge, where ex-Reds teammate Daniel Agger is manager.
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Ovie Ejaria
Brought in on loan from Liverpool in 2018, Ovie Ejaria established himself as a regular starter under Gerrard at Rangers. But the manager was left disappointed when Ejaria opted to cut his stay at Ibrox short that December.
"Am I disappointed he's gone? Yes. Do I think it's the right decision? No, because I think he had an incredible opportunity here. It is what it is. I have to accept the decision. I'm sad about it, I wish him all the best," Gerrard said.
Ejaria joined Reading on loan a matter of weeks later, before spending the following season with the Royals as well. The midfielder made the move permanent in the summer of 2020 and remains with the Championship side, though has only made two appearances this season.
Ryan Kent
Clearly the most successful of Gerrard's signings from Liverpool has been Ryan Kent. After a fine loan spell in the 2018/2019 season, Kent moved to Ibrox in a £6.5million deal in the summer of 2019.
The winger has since established himself as a key player at the Scottish giants, scoring 31 goals and notching 51 assists in all competitions. But he is out of contract at the end of this season, with suggestions that he could look to move on.
Gerrard remains a huge fan of the 25-year-old, with multiple reports claiming he wants to bring him to Aston Villa in January. Kent is expected to line up for Rangers against Liverpool on Tuesday night, a chance for him to test himself against Premier League opposition.
Sheyi Ojo
Attacker Sheyi Ojo arrived for a season-long loan in the summer of 2019, but struggled to establish himself at Ibrox. He scored just five goals during his year in Scotland, before returning to Liverpool.
Ojo paid tribute to the Rangers fans, despite his difficult spell in Glasgow. He wrote on social media: "Best fans in the world no doubt. You guys gave me love and some moments in my life I'll never forget. Thank you."
The Englishman then had loan spells at Cardiff City and Millwall before being released by the Reds in the summer. He returned to the Bluebirds as a free agent, making 12 appearances for the Championship strugglers this term.