Rafa Benitez's battle with Sir Alex Ferguson is long part of Premier League folklore, and it must still grate on the Spaniard that his Liverpool side were pipped to the title in 2008/09.
Manchester United narrowly clung onto the trophy despite losing twice to the Reds that season, and 12 months later Benitez was gone, after his side failed to move forwards.
After spells at Inter Milan, Chelsea and Napoli, where he is still in post, Benitez is expected to be named Real Madrid boss, with the chances described as being 99 per cent by Carlo Ancelotti's agent, reported ESPN.
Regarding Real, The Mirror are already reporting his potential transfer targets, and claim he is eyeing a chance to rip Manchester United's player of the season away from their grasp.
David de Gea has just one year remaining on his contract, and it is reported that Real are 'growing in confidence' they can sign the goalkeeper.
The signing would be a tough if not insurmountable blow for United to recover from, and Benitez would surely relish pulling off such a deal.
One transfer which would create even more personal intrigue is the suggestion he is lining up Liverpool's want away winger Raheem Sterling.
Sterling was Benitez's final gift from Liverpool, convincing him personally to make the switch from QPR's academy to Anfield, where he has become a star.
Benitez can take him away this summer at the right price, and actually solve a huge problem for the Reds in the process. Real would offer a large fee to Liverpool, and be tempting in comparison to Liverpool selling to another Premier League club.
Gone would be the unwanted distraction of a player who does not want to be there, and Sterling would become Benitez's challenge. Where Liverpool go from there, would then be up to them.