Count number of cells from one match to another match on a different sheet

I'm having an issue trying to come up with a suitable formula for a task I need to complete. My Excel is relatively weak and the task is fairly complex!

Below is an example of what I'm trying to accomplish

\1

I have 9 items on "sheet 2"
I would like an "item number" on sheet two to Vlookup that number from sheet 1 I want it to tell me how many cells over it was until it reaches the last data entry in that row and tell me how many cells it was.

If the item is the same as the last entry then return text "correct" and if it doesn't match then return how many behind and red.

I'm guessing some kind of vlookup, and a count with conditionally formatting but no idea how you would find the last data entry and combine this all into one statement and then replicate it down should I want to add say another 500 items.