A spot in the quarter-finals is the reward for the winner of this round of 16 tie and the first leg in Turkey could be crucial ahead of the return meeting at Stamford Bridge on March 18.
Galatasaray and Chelsea haven't met since the 1999/2000 Champions League, but that doesn't stop this being a meeting of old friends and foes. Most obviously, Chelsea come up against one of their all-time great goalscorers in Didier Drogba, who scored the decisive penalty in their Champions League success. The Ivorian is determined not to do his old side any favours. Then there is Jose Mourinho, who comes up against a former colleague in Wesley Sneijder and long-time rival in Roberto Mancini. Every pronouncement that comes from Jose's mouth these days is immediately classified as mind games and analysed intently, even when he doesn't realise he's being recorded. But the Portuguese has had plenty to say about the man who preceded him as Inter boss, and little of it has been complimentary. Of far less importance than all these intriguing sub-plots is a place in the Champions League last eight. We've already seen the benefits of topping the group this year, with five of the six last-16 first legs so far won by the group-winning away sides. Four of those wins have been by two clear goals, with Olympiacos' victory against Manchester United the only success for a runner-up thus far. Chelsea will be hoping to continue that trend but face a Galatasaray side in fine form, sitting second in the Turkish Super Lig behind Fenerbahce and on an 11-match unbeaten run having won their last 10 home games. Big names like Drogba and Wesley Sneijder may attract the headlines, but Burak Yilmaz has been their main goal threat this season. He's scored five in his last six games and has 12 league goals in all.
How they reached the round of 16
Chelsea topped Group E despite losing home and away to third-place Basel - the Swiss side's only two wins in the group stage - thanks to four impressive victories in their remaining fixtures. Galatasaray pipped Juventus to second spot in a group dominated by Real Madrid, a late Wesley Sneijder goal securing a decisive 1-0 win over the Italians on matchday six.
Players to watch
Galatasaray - Didier Drogba
Scored 157 goals in his eight years at Stamford Bridge to lie fourth on the club's all-time scoring charts. His place among Chelsea's greats was therefore already secure before he added the perfect finish, his last act as a Chelsea player being to score the winning penalty in the 2012 Champions League shoot-out victory over Bayern Munich. Now 35, he has scored just six league goals for Galatasaray this season, but is sure to be the man in the spotlight against the club where he achieved so much.
Chelsea - Eden Hazard
Chelsea's standout player this season and sure to be on the player-of-the-year shortlists. While his class has long been obvious, he has clearly stepped up this season to become the main man for a team that often relies on those behind the striker to provide the goals; Hazard's Premier League total of 12 is double that of any other Chelsea player, while he also tops the assist charts with five. If Hazard can be contained, Chelsea's threat is greatly reduced.
Besiktas (home) - won 1-0
Antalyaspor (away) - drew 2-2
Eskisehirspor (home) - won 3-0
Bursaspor (home) - won 6-0
Gazianstepsor (away) - drew 0-0
October 20 1999: Galatasaray 0 Chelsea 5
Chelsea were the last English team to win at Galatasaray, and did so in fine style as two goals from Tore Andre Flo set the Blues on their way to a crushing 5-0 victory in the first group stage of the 1999/2000 Champions League. Gianfranco Zola, Dennis Wise and Gabriele Ambrosetti were also on target. Since that defeat, though, Gala have won three and drawn the other in four home games against English opponents. Chelsea were eventually eliminated in the quarter-finals, while Galatasaray went on to win that season's UEFA Cup.
Do you remember?
The former Inter and Manchester City boss replaced Fatih Terim in the Galatasaray hotseat and managed to achieve what he couldn't at the Etihad in steering his side through the group stages of the Champions League. Given their history and disagreement on who deserves credit for Inter's success under Mourinho, the battle of the managers will inevitably be a key storyline throughout this tie.
The one-time Arsenal man has become a key figure at Galatasaray since his 2011 move and played in all six of their Champions League group games before Christmas. Primarily a full-back in his Arsenal days, Eboue is now deploying his combative efforts in midfield and was on target in his last appearance, a 6-0 win over Bursaspor.
Chelsea are the 21/20 favourites with Sky Bet to claim victory tonight. Gala can be backed at 14/5 and the draw is available at 12/5. Jamie Redknapp's tips are Chelsea to win, Eden Hazard to score first at 6/1 and Chelsea to win 2-1 at 17/2.
We have Andy Schooler's betting tips for the night's Champions League action to check out too. He expects defences to come out on top, with both sides keeping plenty of clean sheets recently and Gala always a tough nut to crack at home.