The current Aston Villa boss endured some cruel moments against the Blues and another one might be around the corner as the Villans host the west Londoners this weekend.
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The 42-year-old played against Chelsea more times than any other side (40).
He was on the winning team 11 times, and though there were some good moments, most of Gerrard's memories against the Blues are probably bad.
But Gerrard also remained loyal to Liverpool as the Blues made serious offers to tempt him into leaving Merseyside.
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During the 2004/05 season, in which the Reds won the Champions League, Chelsea tried everything in their power to buy the Liverpool star.
Jose Mourinho wanted Gerrard and made an offer of £37.5million, which at the time was huge money.
Gerrard later admitted he considered the move because he thought Rafael Benitez wanted to use the funds to build a new squad.
Of course, he didn't go anywhere and has no regrets about that but his record against the Blues has been shocking.
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The former England international scored on his last appearance against Chelsea during the 2014/15 campaign, but that was only his second goal against them.
His other strike came ten years earlier in 2005 in a 4-1 loss.
However, he did manage to score for them in the 2004/05 League Cup final.
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The Blues were trailing 1-0 when Gerrard inadvertently diverted Paulo Ferreira's free-kick into the net to spark a Chelsea comeback that ended with the Blues winning 3-2.
The former Rangers boss was also sent off against Chelsea, and it was a big game as well.
As the 2002/03 season came to a close, Chelsea and Liverpool were fighting it out for Champions League qualification.
The Reds lost 2-1, which was enough for the Blues to claim a spot in UEFA's premier competition at Liverpool's expense, and Gerrard was sent off for two bookings late on.
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But perhaps his worst and the most infamous moment came at Anfield in the 2013/14 campaign.
Under Brendan Rodgers, Liverpool looked on course to win the Premier League, but then Mourinho's Chelsea arrived on Merseyside and everything collapsed.
The score was 0-0 when Gerrard received the ball, but as he went to pass it, he slipped, and Demba Ba raced through and scored.
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Chelsea then added another in the second half after a dreadful Iago Aspas corner triggered a counter-attack that Willian finished off.
Manchester City went on to lift the title and that moment has stuck with Gerrard ever since.
He told The Overlap: "It definitely flashes back, I think the reason why I always say that moment [was his lowest point] is because I don't want people to think I'm ignoring it.
"Unfortunately it happened to me at a real cruel time from a personal point of view.
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"It definitely had an effect on me mentally for some time - I don't know whether it was months or years - still to this day it doesn't feel great.
"Time wise maybe that affected my decision to go to America. I think being in Liverpool, when you're in that routine, sometimes you've got to break free."
And now his job could be on the line as Aston Villa manager as the Birmingham-based club host Chelsea this Sunday.
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Many Villa fans have had enough of Gerrard, with his side struggling to score goals and languishing near the bottom of the table.
If they were to be thrashed by Graham Potter's men, things could turn nasty and Gerrard could find himself out of a job.
However, Villa were expected to lose to Manchester City last month and grabbed a point, so if they can come up with something similar, perhaps Gerrard will avoid more punishment from Chelsea.