Both sides have met 8 times, 4 at the Santiago Bernabeu and 4 at Old Trafford. Both have won 4 games each.
Real Madrid has won 3 out of the last 4 encounters against Manchester United in the Champions League.
Real Madrid won the semifinals of 1956-57 by an aggregate 5-3 margin. First leg at Santiago Bernabeu ended 3-1 and second leg in Old Trafford ended in a 2-2 stalemate.
Manchester United won the semifinals of 1967-68 by an aggregate score of 4-3. The first leg at Old Trafford ended 1-0 and the second leg in Santiago Bernabeu ended in a 3-3 stalemate.
Real Madrid won the quarter finals of 1999-2000 by an aggregate score of 3-2. First leg at Santiago Bernabeu ended in a goalless stalemate and the second leg at Old Trafford was won by Madrid with a 3-2 margin.
Real Madrid won the quarter finals of 2002-03 by an aggregate score of 6-5. They won the first leg at Santiago Bernabeu by a 3-1 margin and lost the second leg at Old Trafford by a 3-4 margin.
Ronaldo (Brazil) has scored the only hat-trick for Real Madrid in meetings between these two sides in the 2002-03 second leg quarter final at Old Trafford which they lost to Manchester by a 3-4 margin but due to those three away goals they became through to the semis.
Manchester United last beat Real Madrid in the 1967 Semi Finals.
Real Madrid have won the Champions League 9 times which makes them the most successful club in Europe while Manchester United have won it 4 times.