TR's Model 1895 was a commercial model - serial number #7588.
Before everyone races out to buy a Winchester Model 1895 for 'their' version of a Spanish American War military rifle - 'The Winchester Book' - by Madis - has this observation on page 481.
"Winchester had great difficulty in getting the adoption of the Model 95 by the Army. Upon the recommendation og General Miles, Commander of the Army, an order of 10,000 muskets was placed with Winchester in May of 1898. The Ordnance Corps was having difficulty in repair and maintenenace of the huge variety of arms already in use by the armed forces at that time: the demand for arms and ammunition was heavy due to the demands of the Spanish American War.
When the component parts and muskets had been inspected by the the army inspectors at the Winchester factory, a large number had been rejected for unsubstantial reasons. After some discussion, the 10,000 muskets passed inspection. In 1899, one hundered of the muskets were issued to the Philippines, but the Ordnance Board there gave an unfavorable report and the one hundred muskets were returned to the United states and were sold to a boston arms dealer. The remaining 9,900 were sold to a New York dealer, who shipped them to Cuba in 1906."
Commercial Model 1895 Winchesters were available - but there weren't 'issue' carbines, since the Model 95 that was contracted for was the Musket.
When the Contract was let in May, 1898 - the Rough riders were then in San Antonio, and by August of that year, were aboard the transport 'Miami' - steaming out of Santiago Channel, on their way to folding their flags on September 15, 1898.
The Winchester drama would play itself out while they were operational, and issued with Krag carbines.
Vaya,
Scouts Out!