The Champions League holders were left on the brink of being knocked out of the competition thanks to a 3-0 defeat in Turin against Juventus.
Add that to a run of domestic form which has seen the Blues win one game in their last five league matches and Chelsea now begin the familiar process of searching for a new manager.
|Next Permanent Chelsea Coach
|Odds from William Hill
Former Barcelona coach Pep Guardiola, who is currently on a footballing sabbatical after leaving the Catalan giants in the summer, is the next in the market, priced at 7/4 (2.80) with William Hill.
The 41-year-old has been linked with a move to Stamford Bridge in the past few months but questions remain over whether he would consider taking such a position so soon, especially given his comments about wanting more time away from the game.
Given the pressure that comes with this particular role and the reasons he cited for leaving Barcelona, it seems that the 7/4 (2.80) available is too short a price to be backing him at this stage.
Harry Redknapp is available at 5/1 (6.0) to succeed Di Matteo and would be immediately available after leaving Tottenham at the end of last season, which could be an important factor in any new appointment given the hectic schedule of games coming up for the London club.
Former assistant coach Steve Clarke, who worked closely with Jose Mourinho during his time at Stamford Bridge, is a 10/1 (11.0) shot to take over after making an impressive start with West Brom in his first season at the Hawthorns.
Everton boss David Moyes is priced at 16/1 (17.0) with William Hill while Fabio Capello, Guus Hiddink, Jose Mourinho and Laurent Blanc are all 25/1 (26.0) outsiders.
For punters, managerial markets are notoriously difficult to predict, but the list of credentials needed to take the reins at Stamford Bridge under Abramovich's watchful eye mean relatively few candidates fit the bill.
Benitez seems the logical choice especially given the timing which may effectively rule out Guardiola, who may have been more welcoming to an approach in the summer. At 10/11 (1.91) Benitez would seem to be the ideal candidate and that price will not last long.
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Jim Knight is Betting Editor at Goal.com and has been tipping football games since he was old enough to place a bet. He is a Leicester City fan, writer and member of the We Are Going Up Podcast
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