Carlo Ancelotti seems destined to shape Liverpool's history as an outsider. The Italian has never managed the Reds but throughout his managerial career, he's had a notable impact on their fortunes.
Liverpool's most famous night happened in Istanbul, with Ancelotti in the opposing dugout while in charge of AC Milan. He was linked with replacing Brendan Rodgers in 2015, but the club instead opted for Jurgen Klopp and haven't looked back since.
He was even in charge of Everton when the Blues finally managed to end their Anfield hoodoo last season, winning 2-0 in an empty stadium. On Saturday night, he will face Liverpool in yet another European final, it will be his third bout with the Reds on the grandest stage.
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Ancelotti also has a curious history with Klopp. The German coach is regarded as one of the world's best and few have been able to compete with him over the years, but the current Madrid boss has a relatively strong record against his sides.
The pair have clashed 10 times in total, with Klopp winning just three. Ancelotti has four wins under his belt, with the rest ending in draws.
Klopp has averaged around 1.2 points per match against the 62 year-old, which is lower than his averages against the likes of Pep Guardiola, Thomas Tuchel, Jose Mourinho, Jupp Heynckes, Arsene Wenger and Mauricio Pochettino.
Klopp's preference to stick with a go-to system never seems to help his cause against Ancelotti, who tends to deploy his players to counteract Liverpool's favoured 4-3-3. The Italian tactician is a master of generating strategies for isolated matches. Unlike Klopp, he doesn't represent one fixed formation or philosophy.
He is always adapting. His infamous Milan side adopted a midfield diamond for the most part. His Paris Saint-Germain team formed a 4-3-3 shape. Napoli used 4-4-2 under his guidance and during his first spell at Madrid some years ago, they used 4-2-3-1 most often.
The three-time Champions League winner is more in the mould of Rafa Benitez than Klopp, having approached matches almost like they are conducted on a chess board rather than a football pitch. Few managers are as effective as Ancelotti when it comes to navigating knockout matches and using substitutes to change the course of a game, just ask Chelsea and Manchester City.
"Liverpool have enormous quality but they become more controllable when they are forced to play in tight spaces," he said after securing a draw at Anfield with Napoli in 2019.
During his time in charge of the Serie A outfit, Ancelotti faced Klopp four times in the Champions League and lost just once. His defenders in particular demonstrated a tendency to get tight to the likes of Mohamed Salah, Sadio Mane and Roberto Firmino, often forcing them to lose possession or pass backwards.
Klopp will have to be prepared this time around. He will likely stick with 4-3-3, but the way in which his players behave within the confines of that system has to be unpredictable. Otherwise, Ancelotti has proved he's capable of devising a plan to highlight the flaws of the Reds.
Ultimately, the Liverpool boss will need a few aces up his sleeve if he's to begin improving his record against his upcoming opponent.
