1. Real Madrid vs Liverpool
Looking at all the runner-ups of their groups, Real Madrid are by far the strongest team in there. They have an unmatched European pedigree and despite missing Cristiano Ronaldo, are still a strong enough outfit to compete for the continental crown, like in the very recent history. Zinedine Zidane became the manager of Los Blancos at the start of 2016 and won the Champions League three times in a row, before leaving the club in 2018 and re-joining the Bernabeu in 2019. That means he is unbeaten in European knockout ties as Real Madrid manager.
Another manager who is unbeaten in European knockout ties in his current role, albeit only two-legged ones, is Jürgen Klopp. He took Liverpool to one Europa League final and two Champions League finals, winning the second one. The first one was a painful defeat to Zidane's Real Madrid in 2018. Two horrific errors from Loris Karius handed the trophy to the La Liga side. The following year, the Reds won the biggest prize in club football and are currently the best team in the world, based on the year they have had.
There is some unfinished business for Mohamed Salah and co, especially after Zidane joked that Real Madrid 'will eliminate' Liverpool. The Reds will be determined to avenge that painful defeat in Kyiv, en route to what would be a third consecutive Champions League final. The two European giants did play each other in the 2008-09 Champions League Round of 16, with Liverpool thumping Real Madrid 5-0 on aggregate.
This is easily the most exciting match-up that could come out of Monday's Champions League last 16 draw. Either side could potentially lose their first two-legged European knockout tie, either Klopp or Zidane.