Another defeat for the Blues as their disappointing USA pre-season tour came to an end.
At least this time it was not the might of the MLS all-stars with over the hill players embarassing the European Champions, but AC Milan, a genuine world force in football.
A second-half strike from Milan’s Urby Emanuelson in the early hours of Sunday was enough to send the boys home with their tails between their legs.
The wide midfielder tucked home on 68 minutes in the Sun Life Stadium in Florida and deserved their victory.
But it had started well foer the Blues and John Terry had the first effort of the game on seven minutes, but he scooped the ball over the Milan crossbar from an unmarked position, 10 yards out, after a good header from Branislav Ivanovic.
With Chelsea dominating the midfield area, Milan was content to defend deep and look to attack on the counter.
And it took the Italians until the 27th minute for a shot to be directed towards Petr Cech.
It came from the right boot of Bakaye Traore on the edge of the Blues’ penalty area. But the ball zipped wide of Cech’s left upright.
Kevin Prince-Boateng followed that up with a right-footer of his own a minute later, signalling that the Rossineri were getting a foothold into the game.
Ten minutes before the break saw another counter by Milan resulting in Stephen El Shaarawy letting fly from 30 yards – but it failed to trouble Cech who gobbled it up.
Frankly nothing much else happened for the remaining of the half, Chelsea certainly dominated the opening periods of the first 45 minutes but Milan finished stronger, but neither goalkeeper had a shot worthy of the name to save.
Marko Marin replaced Raul Meireles at half time, allowing Hazard to move further central with Marin going out wide on the left.
The positional change for Hazard almost reaped instant rewards with the Belgium midfielder instrumental in creating several quick-fire attacks. The second of which almost saw Mikel rifle home from 20 yards, but Milan goalkeeper Marco Amelia was equal to the task.
But Milan’s counter-attacks saw Urby Emanuelson force Cech into a diving save on 52 minutes.
Chelsea tried a counter of their own two minutes later with Chelsea first shot on target from Frank Lampard - Amelia, like Cech before, snuffled the right-footer.
Fernando Torres entered the fray on 60 minutes, replacing the ineffectual Romelu Lukaku; Paulo Ferreira took the place of Cole with Gary Cahill replacing John Terry.
But the changes did not improve things and the Blues went behind on 67 minutes when yet another Milan counter-attack saw Emanuelson tuck home from close range.
The third set of substitutions, all pre-arranged saw Michael Essien, Sam Hutchinson and Florent Malouda come on for the final 14 minutes.
Of went, Lampard, Ivanovic and Ramires.
A Hazard free-kick on 86 minutes was a great chance to salvage a result for the European Champions, but the only danger was to the spectators in row Z.
The Blues now need a significant improvement in form if they are not to suffer further embarassment when they face, on Saturday', a trip to the south Coast, and a match against Brighton and Hove Albion.
Blues boss Roberto Di Matteo said afterwards, “We were well organised and pressed well.
“We made a mistake for their goal and lacked a cutting edge (up front) – we missed the final pass.
“We have not created many chances in front of goal and we have to improve on that.”
But the manager insisted there were some positives: “It’s important that more players got more minutes on the pitch and we came away without any injuries.”
Teams: Petr Cech; Branislav Ivanovic, David Luiz, John Terry (c), Ashley Cole; John Mikel Obi, Frank Lampard; Ramires, Eden Hazard, Raul Meireles; Romelu Lukaku.
Subs: Jamal Blackman, Paulo Ferreira, Sam Hutchinson, Nathaniel Chalobah, Gary Cahill, Michael Essien, Marko Marin, Florent Malouda, Lucas Piazon, Fernando Torres.
AC Milan: Marco Amelia, Luca Antonini, Mario Yepes, Daniele Bonera, Djamel Mesbah, Massimo Ambrosini, Bakaye Traore, Mathieu Flamini, Kevin Prince-Boateng, Urby Emanuelson, Stephen El Shaarawy
Subs: Mattia De Sciglio, Antonio Nocerino, Francesco Acerbi, Riccardo Montolvio, Ignazio Abate, Bryan Cristante, Simone Andrea Ganz, Mattia Valoti, Edoardo Pazzagli, Philipp Prosenik, Antonio Cassano.