Can I do a tax free rollover for $10,000 from a Roth IRA that I’ve had for over 5 years with company A, but rolled it over to company B in 2019? My first contribution with company B was over 5 y

[Critter]

There are no restrictions on moving any IRA money from one company account to another. 

[dmertz]

... except that if moved by 60-day rollover only one such IRA-to-IRA rollover is permitted in any one-year (365-day) period.  If instead the account is moved by non-reportable trustee-to-trustee transfer (neither a distribution nor a rollover), there is no limitation.