Negative.
If I went strictly by what the IRS has (1099’s) as I do not have canceled checks/invoices to write off - I’d be screwed into the next dimension.
Based on some online research -
"The good news is that the IRS does not require you to go back 20 years, or even 10 years, on your unfiled tax returns.
In most cases, the IRS requires you to go back and file your last six years of tax returns to get in their good graces. And then, to make arrangements on payment of what is owed.
The six year enforcement period for delinquent returns is found in IRS Policy Statement 5-133 and Internal Revenue Manual 1.2.14.1.18."
Based on that - Im not going to go back 20 years to file those returns. I have been up-to-date and filed on time for the last decade however.