<p>Let me just say this. If this is Rinnegan Madara, Itachi gets destroyed. If this is EMS Madara, Itachi loses with low difficulty. If this is MS Madara, Itachi loses with mid difficulty. Sharingan Madara clearly loses to Itachi though. Based on what is stated about Tsukuyomi, it will work on Madara if he gets caught. Only a immediate blood relative can break it, as seen with Sasuke. Plus Madara's genjutsu pales in comparison to Itachi's. Itachi does have the Yata Mirror and Tostuka Blade which can be helpful against Madara, but it wouldn't change the inevitable. Madara's has enough stamina to outlast him and that's what it going to come down to with MS Madara at least.
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