It has been claimed that the duo's meeting in the tunnel during the Red Devils' pre-season tour of the US was the first time they had spoken to each other in 17 days.
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The two were seen shaking hands inside the Hard Rock Stadium after the 2-1 victory against Real Madrid.
But with Mourinho disappointed over a lack of signings at Old Trafford, the relationship between him and Woodward is believed to be at an all-time low.
A source told the Daily Mail: "It was as if Ed realised that he had to do more, but it was too little too late.
"Everyone could see that Jose was completely mystified by Ed's absence.
"He's never experienced that before with a chairman on tour. Jose was miserable in the US but people began to see that he had a point."
The Special One is understood to have been upset after going on a pre-season tour with an inexperienced squad, while he has been vocal in his quest to sign two more players.
United have already landed Fred, Diego Dalot and Lee Grant this summer, but Mourinho is keen on more recruits as he looks to cut the gap on rivals Manchester City.
A centre-back is believed to be the top priority for the ex-Chelsea gaffer, with Harry Maguire, Yerry Mina and Toby Alderweireld all linked with the FA Cup runners-up.
Speaking recently, Mourinho said: "I would like to have two more players. I think I am not going to have two, it is possible I’m going to have one.
"I gave a list to my club of five names a few months ago and I wait to see if it’s possible to have one of these players.
“If it is not possible we keep fighting and working and believing in the players that we have.”
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