1. RB Situation
As of now Branislav Ivanovic is Chelsea's starting RB and that doesn't seem to be changing anytime soon. Ivanovic is a very capable defender and has played very well, but there is a huge doubt on whether or not he can keep up with EPL wingers such as Gervinho and Valencia. This was very clear in Chelsea's match against Reading when there pacy wingers ran at the Serbian. Chelsea needs to look at other options at right back, maybe even play Ryan Bertrand there because there his no way Ivanovic can shut down the leagues speedsters.
2. Luiz or Cahill
John Terry is Chelsea's first choice on the back line every match, no questions asked, but who will be playing beside him is still in doubt. The Blues have to very good options beside Terry which can be seen as a good problem. David Luiz has the talent to be a world class defender but doesn't seem to want to stay back and Gary Cahill his almost a mirror image of a young Terry on the pitch. Right now Cahill has to be the choice, he has looked very good in the match time he has had and he can be one of the league's best defenders and he is starting to look like Di Matteo's first choice.
3. What to do with all the Midfielders
Chelsea look like they have gotten one of the best transfer prizes in the history of the English League with Eden Hazard and he will start every match he is fit. Frank Lampard and Juan Mata will most of the time be by his side, but with the formation Di Matteo has used who will fill the other spots? Ramires hasn't looked half the player he was last year and it looks like Sturridge, if he stays, might want to try out the winger role everyone at Stamford Bridge is looking for. This all being said Chelsea just spent 25 million Euro on young Brazilian Midfielder Oscar, and he needs to start. Di Matteo needs to play Oscar in every match and get him as many starts as he can, he is the next big thing and is a big part of his future. I see Matteo Giving Oscar and Sturridge both starting roles and letting Mikel hang back with Lampard.