The former Liverpool boss was approached twice to return to the club he used to work at as the 'B' side's coach.
Benitez was approached twice in 2008 and in 2009 to join his former club as their new boss - during a time when the Spanish giants were struggling to find the right man to take them forward.
His agent Manuel Garcia Quilon said: "Rafa was for two consecutive years given the chance to become coach of Real Madrid.
"We received a very interesting proposal from the Blancos five years ago and the year before that.
"In order to convince him to accept the offer, Florentino Perez flew out in person with a private jet to England.
"He tried, without success, to convince Rafa's wife Montse to follow her husband in this new adventure.
"However, as Rafa had just renewed his contract with Liverpool and is a man of his word, he turned down the offer from his beloved Real Madrid despite the fact it was the best economic and sporting proposal he'd ever received."
It also showed the considerable bond that both Benitez and his wife had with Liverpool given the club was owned by Tom Hicks and George Gillett at the time - who were not well liked by the Reds' fans for several reasons. They had also previously offered Benitez's job to Jurgen Klinsmann prior to the Spaniard signing the new contract at Anfield.
Funnily enough the two sides in 2009, and it was Liverpool who were victorious in a 5-0 aggregate victory in the last-16 stage of the Champions League.
But now, there could be a feeling of 'what could have been' given Real's rapid progress since which has seen their progress of late culminate in winning the Champions League last season - whilst shortly after being approached for a second time, Benitez was sacked as Liverpool manager in 2010.
Since then, he had an unsuccessful spell in charge of Inter Milan, but to an extent rebuilt his reputation since by winning the Europa League at Chelsea, and the Coppa Italia in his first season at Napoli.