Comprising the majority of the Earle D. Gregory collection are military records and files dating back to when Gregory was a member of the 1st Virginia, 29th Regiment during World War I. This material consists of publications and correspondence pertaining to Gregory's infantry unit, more specifically Gregory's impact during his first day of combat at Bois-de-Consenvoye, France for which Gregory was awarded the Congressional Medal of Honor for his heroic actions. Significant material from Gregory's affiliation with the Medal of Honor is also included, such as invitations to Gregory's ceremony and various correspondence, along with several pictures taken from the ceremony, including one photograph with Earle Gregory and President John F. Kennedy.

Also included in the Gregory collection is material from VPI where Gregory enrolled after he came back from his service in France. Most of the material is comprised of correspondence and alumni bulletins, along with some photographs taken of Gregory while he was a student and his original student transcript.

In his lifetime, Earle Gregory received several awards and recognitions. Some of the most notable awards include the Medal of Honor and Purple Heart, along with a Medal of Honor plaque signed by President Lyndon Johnson, which is a replacement of Gregory's original certificate signed by President Woodrow Wilson which was destroyed in a fire. A total of eleven medals are included in the collection, along with other certificates and miscellaneous items, including a signed invitation to President Richard Nixon's inauguration.