Medicare does not recognize 99255 because that is a consultation code, but aside from that, you are allowed to bill critical care and an E&M service on the same date under the following circumstance:
When a hospital inpatient or office/outpatient evaluation and management service (E/M) are furnished on a calendar date at which time the patient does not require critical care and the patient subsequently requires critical care both the critical Care Services (CPT codes 99291 and 99292) and the previous E/M service may be paid on the same date of service.
You'll find this guidance in the Medicare Claims Processing Manual, Chapter 12, section 30.6.9 A. - Hospital Visit and Critical Care on Same Day, which you can find here:
For non-Medicare insurance plans, you would need to review the policies of the specific payer you are billing.