Shane Long, currently in unplayable form, set the ball rolling on what could be miserable week for Di Matteo when he ripped Chelsea's powder puff defence apart on Saturday and teed up West Brom for a famous victory.
In the aftermath, Petr Cech lost his cool with his misfiring team mates amid rumours of dressing room unrest.
To cap it all, it is expected that the English FA will drop their investigation into race row referee Mark Clattenberg, leaving Chelsea open to ridicule and possible disciplinary action.
And if Chelsea fail to get a result against Juventus in Turin tomorrow night, Roman Abramovich's grip on the Champions League will be short-lived.
If all that wasn't enough, Di Matteo must also find a way to beat league leaders Manchester City when they travel to Stamford Bridge next Sunday.
With just two points to show from their last four Premier League fixtures, it could be a tall order for the struggling Blues.