Jordan Henderson is set to face his former club Liverpool again when Chelsea travel to Anfield for a Carabao Cup fourth-round tie on Wednesday night. The 36-year-old midfielder, who joined Chelsea on a free transfer this summer, spent 12 years at Liverpool and captained the side for the last eight of those years.
Henderson left Liverpool in 2023 to sign for Saudi Pro League side Al-Ettifaq, but his time in the Middle East lasted only six months before he returned to Europe with Ajax. An 18-month spell in the Eredivisie ended in May 2025, after which he signed for Brentford and helped the Bees to a ninth-placed finish last season.
A Lifelong Connection to Liverpool
Despite the rivalry between Liverpool and Chelsea, Henderson has made clear that his affection for Liverpool is enduring. In an emotional statement posted on social media after his departure more than three years ago, he wrote: "It's hard to put these last 12 years into words and it's even harder to say goodbye. I will always be a Red. Until the day I die. Thank you for everything. You'll never walk alone. Jordan."
His most recent visit to Anfield came on the final day of last season, when Brentford held Liverpool to a 1-1 draw. Earlier in that campaign, in the reverse fixture at the Gtech Community Stadium, Brentford beat Liverpool 3-2, condemning the away side to a fourth straight loss.
Facing the Reds Again
After that match, Henderson spoke openly about his feelings for Liverpool: "I was there 12 years, dedicated a lot of my life. My kids were born there, so it holds a special place in my heart. I still want Liverpool to do well - of course not when we're playing them, but overall - and that'll never change."
He added: "And the fans have always been amazing, and it was special just to see a few of them. I know they probably left a bit early because of the result, but it was nice to see them again."
A New Chapter at Chelsea
Henderson has started four Premier League matches for Chelsea this season, scoring two goals and providing one assist. Speaking about his move, he said: "I'm enjoying the challenge. I think a lot of people spoke about the move when I came but for me I've just got to do my talking on the pitch."
He continued: "It helps when you're playing with top players around you and I feel like the team's really coming together. I don't really think too much about what other people say. I have just as important a role as every other player on the team, I've just got to bring whatever I bring."
Henderson also acknowledged the value of learning from younger teammates: "But they also help me as well. It's not all me coming here to help younger players, younger players can also help experienced players. I'm still learning, and I'm still improving."
On external criticism, he said: "There are going to be so many different opinions I just try and use it as fuel, use it as energy, to prove people wrong again. I just want to do my business on the pitch. That's where I do the talking really."
