José Mourinho's 4 most humiliating defeats as a Manchester United manager

#1 Manchester United 0-4 Chelsea (2016/17 Season)

Conte, with his celebrations, managed to worsen Mourinho's bad day at the office

The first time Mourinho returned to Chelsea as a United manager, was also his most humiliating time as the Red Devils boss. United were riding high after a midweek home win over Fenerbahce in the Europa League and on 23rd October 2016, Jose Mourinho took his Manchester United side to the Stamford Bridge.

The Portuguese started with De Gea in goal and Blind, Smalling, Bailly, Valencia in defence. Herrera started as the deep-lying midfielder, with Fellaini alongside him. Pogba started in an advanced role, along with Lingard and Rashford. Ibrahimovic led the line for United. Wayne Rooney missed the trip through injury.

Yet, it was the most unceremonious of starts for the Red Devils. Within the first 30 seconds, Pedro had put Chelsea ahead, without the United defence even touching the ball. Smalling’s hesitation allowed Pedro to round De Gea and send Stamford Bridge and Conte in a frenzy. Cahill doubled the score in the 21st minute, after some disgraceful set-piece defending from United. The first half ended 2-0, with United and Mourinho looking clueless.

The second half did not see any improvements from United and Hazard capitalized on more defensive errors to put Chelsea 3-0 up in the 62nd minute. Kante set the Stamford Bridge roof off when he scored Chelsea’s fourth goal in the 70th minute. United already looked defeated and somehow managed to complete the game without conceding further.

While the defence was blamed, United were also blunt in attack – they had 16 shots and none of them was on target. It was a poor day for Mourinho as he watched Conte and the home fans “celebrate like crazy kids” again and again and again.

It was Mourinho’s biggest defeat as a United manager and against his old side, at their ground, in front of their supporters, it was his most humiliating defeat as well.