Roman Abramovich has told the club that no player in their 30s will be offered longer than a one-year deal, which could spark an exodus of ageing Chelsea stars.
The Sunday Mirror reports how the Russian owner delivered the warning as senior pros like Frank Lampard and Ashley Cole continue to hold out for longer-term deals that will keep them in west London.
With both players out of contract next summer, failure to agree new contracts will leave them free to speak to foreign clubs in January.
It's a stance that has already led to the departure of Didier Drogba, who swapped Stamford Bridge for Chinese outfit Shanghai Shenhua in May.
There will also be doubts over 31-year-old Chelsea captain John Terry, whose current deal runs out in 2014.
Roberto Di Matteo wants to keep both Lampard, 34, and Cole, 31, but knows that he faces an uphill battle to convince them to pen a short-term agreement, especially as they are each likely to have a number of other offers.
Lampard is a target for MLS side LA Galaxy, who are prepared to give him a two-year deal, while Cole is wanted by big-spending Paris Saint Germain - now managed by former Chelsea boss Carlo Ancelotti.