Putting together a deal list for someone mid-senior / senior

I am looking for jobs. I have been out of undergrad since 2012 and MBA since 2018. 

My resume is restricted to one page which I send out with any cold emails. Most of my resume is taken up by my current job, where I have been for nearly 4 years. I was recently advised to start including my full deal list (with my resume), which is about ~25 to 30 deals since I joined the workforce 

Many of my deals did not close / get announced, but I was a key part of them and they at least went to Round 2, which is why I included them. Many deals are ten plus years , where I barely remember info on the deal specifics, but know enough to talk about business models 

My question to this forum is: 
1. how should my deal sheet be structured? I can't devote more than a single line to each deal, otherwise I'd easily go beyond one page 

I am breaking them down by sectors that I have covered since 2012. Should I just include the cheque sizes / deal list?

2.  When you're including a full deal sheet, is it fair game to be asked to speak about something from five plus years ago?