Chelsea will host Milan on Wednesday in what could well be a must-win fixture for the Blues, who sit last in Champions League Group E.
England has not been a happy hunting ground for Milan, but the group leaders and reigning Serie A champions will be hoping for a change of fortune when they roll into Stamford Bridge.
Meanwhile, Mykhaylo Mudryk will get a chance to show why he is considered one of the top young talents in Europe as Shakhtar Donetsk head to the Santiago Bernabeu to take on Real Madrid.
Paris Saint-Germain will look to change their poor historical record against Benfica, with Kylian Mbappe on the brink of becoming the club's record European goalscorer.
Stats Perform has dug up the most interesting facts and angles for each contest on Wednesday.
Chelsea v Milan
This is the first time these two teams will meet in the Champions League since they were in the same group in 1999, with both of those matches ending in draws. They have not met in a competitive game since, with all four of their 21st-century contests coming in the International Champions Cup (Chelsea won three of those with Milan recording one victory).
Chelsea have only lost twice at home to Italian teams in continental competition, collecting eight wins and three draws. They lost to Lazio 1-2 in 2000, and to Inter 1-0 in 2010.
Milan's record in England also gives no reason for optimism, with only one win from 20 tries in European play (D7 L12).
Olivier Giroud was subbed off in Milan's dramatic 3-1 win over Empoli on Saturday. The France striker could become the 10th player to score for and against Chelsea in the Champions League, and first since Loic Rémy for Lille in December 2019, should he net in this meeting.
Real Madrid v Shakhtar Donetsk
This is the third consecutive season these sides have met in the group stages. It is the fifth time teams have ever been paired together in three consecutive seasons, and Shakhtar was involved in the most recent occasion as well, against Manchester City from 2017-18 through to 2019-20.
Over the past two seasons, they have split the wins evenly, with Shakhtar winning both games in the 2020-21 campaign, before Madrid triumphed in both fixtures last season.
After a win and a draw in the first two matchdays, Shakhtar boast the highest shot conversion rate in the competition, scoring with five of their 10 shots, including two goals from 21-year-old rising star Mudryk.
On the other side, Vinicius Junior leads the Champions League with 33 chances created and seven assists from open play since the start of last season, and he shares the mantle for most goal involvements at 18 with Barcelona's Robert Lewandowski.
Benfica v Paris Saint-Germain
Benfica are looking to extend their surprisingly strong record against Paris Saint-Germain, having won three of their six previous meetings (1D 2L) in European competitions, including the past three in a row. Their last fixture came in the 2013-14 season, with Benfica winning 2-1 at home.
In fact, Benfica have enjoyed plenty of success while hosting French sides, with five consecutive home wins – twice against Lyon, as well as beating Lille, Monaco and PSG.
However, PSG are a different beast now then they were back in 2014, and have only lost one of their past 11 matches in the group stage (8W 2D).
At only 23, Mbappe can become the club's all-time leading scorer in European competitions with one more goal. He is currently tied at 30 with Edinson Cavani.
RB Leipzig v Celtic
These sides both won their home fixtures when they were matched up in the 2018-19 group stage, and they will be desperate for a result as they enter Wednesday's game with only one point between them in Group F.
Celtic will be looking to make history as they have never won a European game away in Germany (10L 3D), failing to score on nine of those 13 occasions.
But it might be a case of a stoppable force meeting a movable object, as Leipzig have not kept a clean sheet in their last seven home games in the competition. They have only shut out their opponents twice from 15 Champions League home games.
Jota will be the key for Celtic's chances, with his six chances created trailing only Napoli's Piotr Zielinski (eight), while only Madrid star Vinicius is credited with more take-on dribbles (11) than Jota's nine.
Other fixtures:
Manchester City v FC Copenhagen
23 – Manchester City are two games away from tying Manchester United's record of 23 consecutive Champions League home fixtures without a loss. They are unbeaten at home in the competition since 2018.
62 – City's Erling Haaland averages a goal every 62 minutes in the competition, netting 26 goals in 21 appearances. He is well clear of second-placed Mario Gomez, who scored his 26 goals on an average of every 102 minutes.
Sevilla v Borussia Dortmund
1 – Borussia Dortmund have only won one of their past 11 trips to Spain in the Champions League (L7 D3), but that win came from their most recent opportunity, against Sevilla in February 2021.
3 – Sevilla have failed to score in each of their past three Champions League games. They have never gone four consecutive games in European competition without scoring.
Juventus v Maccabi Haifa
29 – It has been 29 years since Maccabi Haifa defeated an Italian team in European competition (3L 1D), with their only victory coming in 1993 against Parma.
8 – The Israeli side have lost all eight of their Champions League fixtures since 2002, by a combined aggregate score of 13-1.
Salzburg v Dinamo Zagreb
6 – Salzburg can become the first Austrian team to ever go six games unbeaten in the Champions League if they can avoid defeat against Dinamo Zagreb, with three wins and two draws from their past five.
23 – The last time Zagreb kept a clean sheet away from home in this competition was 23 years ago, drawing 0-0 against United at Old Trafford in 1999. Since then, they have conceded 52 goals in 18 away games (2.9 per game).
Al-Riyadh 2-2 Al-Nassr: Laporte sent off for punch as Al-Nemer salvages point
Former Manchester City defender Aymeric Laporte was sent off for punching Mohammed Al-Aqel on the arm as Al-Nassr played out a 2-2 draw with Al-Riyadh in the Saudi Pro League.
Meshari Al-Nemer's 97th-minute strike salvaged a point for Al-Nassr, who had trailed for over half the game and played with a one-man disadvantage for over half an hour.
Otavio had put Al-Nassr ahead only for Andre Gray to drag the hosts level, before Al-Aqel gave David Ospina no chance with a terrific overhead kick to make it 2-1.
Al-Nassr's position was put in further jeopardy when Laporte was sent off following a bizarre off-the-ball incident which saw him grab and punch Al-Aqel on the elbow, while Cristiano Ronaldo came up with a glaring miss from Sadio Mane's pass across the six-yard box.
Al-Nemer levelled at the death for Al-Nassr, though they still sit some 14 points adrift of champions Al-Hilal, who could complete an unbeaten season against Al-Wehda on Monday.
Data Debrief: Laporte's horror show
It was a game to forget for Laporte, whose bizarre punch on Al-Aqel put Al-Nassr up against it versus a team still in danger of relegation.
Laporte did not attempt a single tackle in the game while his four duels contested were the joint-fewest of every outfield starter (alongside Khalid Al-Shuwayyi). He was also sent off in Al-Nassr's AFC Champions League quarter-final tie against Al Ain in March.
Bologna confirm Motta departure with Juventus move imminent
Bologna have confirmed head coach Thiago Motta will leave the club at the end of the season, with the former midfielder expected to take over at Juventus.
Motta has overseen an incredible season for the Rossoblu, who have clinched a top-five Serie A finish and Champions League qualification with one game remaining.
He has been touted as a leading contender to succeed Massimiliano Allegri at Juventus, after he parted company with the Bianconeri in the aftermath of last week's Coppa Italia triumph.
Motta's move to Turin now appears imminent after Bologna announced he would not be extending his contract on Thursday.
"In the past two years, I have got to know a well-prepared and winning coach," club president Joey Saputo said in a statement.
"He has instilled a brilliant style of play in this time. Reaching the Champions League means he and all these players will go down in our club’s history.
"I would have liked him to stay at Bologna but I can only ever thank him and his staff for these amazing two seasons and I wish him the best for the future."
Bologna face Genoa – with whom Motta started his senior managerial career – in their final game of the season on Friday, knowing a victory will guarantee a top-four finish.
Postecoglou: There's a deadline on signing Werner
Ange Postecoglou has revealed Tottenham have a deadline if they want to make Timo Werner’s loan deal permanent.
The German joined Spurs on loan in January from RB Leipzig, scoring twice and assisting three goals in 14 matches in all competitions for the North London side.
However, Werner missed the last five games of Spurs’ season due to a hamstring injury he sustained against Arsenal.
Postecoglou admitted that he was relaxed about the situation, but whether a deal was made was out of his hands.
Speaking to reporters following their friendly in Melbourne against Newcastle United, Postecoglou said: "I think from our perspective, there's a deadline there.
"Again, a lot of that will depend on the negotiations between the clubs and how Timo feels.
"Again, from my perspective, I'm comfortable with that situation, and I'll let the other guys steer it to see what kind of outcome there is."
After a strong start to their season, Spurs eventually finished fifth in the Premier League, securing a place in the Europa League next season.
The Australian also believes the club need to bring more attacking players in as a priority to balance the higher workload next season after struggling with injuries this campaign.
"Yeah, absolutely. It's no secret [we need new forwards]. You saw the way we finished the season," he said.
"We obviously lost Richarlison and Timo Werner as well with injuries, but we're fairly light in that area.
"We started last season with Manor [Solomon] and [Ivan] Perisic, and we were quite healthy in that front third in terms of numbers, but as the year went on it became pretty evident that we needed to bulk up.
"We're in Europe as well next year, so we'll have more games, and it's definitely an area of the park we'll need to strengthen."
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