The most notorious failures of Real Madrid in the Cup

4. 2000-01 | 1/32 final | Toledo 2 – Real Madrid 1

Madrid's rival was Toledo, recently relegated to Second B after living his golden age with seven consecutive seasons in Second in which they were even about to go up to First under the hand of Gregorio Manzano. After a quarter of an hour, the locals were already winning with goals from Israel and Cidoncha. Savio closed the gap in the 19th minute, but Madrid, with many substitutes, was unable to come back. The whites learned their lesson and in the following seasons they did not allow Pájara Playas, Lanzarote, Sanse on two occasions or Leganés on two other occasions to give the surprise.