The original SH-48 State Highway 99 traces its roots back to the first
State Highway 48, which was first established on January 19, 1927. This highway connected Ada to
Holdenville; it roughly followed present-day SH-99 until about north of the
Canadian River, it then turned east and passed south of the unincorporated town of Vamoosa, after which it followed the route of today's SH-56. After , it passed through Sasakwa, in which it turned north and ended at the original SH-3, at the intersection called "Five-Mile Corner", west of Holdenville. The 1928 state highway map shows the highway extended to SH-9 (now US-62) near Prague along the present-day SH-99 alignment, with the Canadian River crossing as a toll bridge. By January 1, 1929, the route had been realigned to pass through
Konawa. The old designation between the Canadian River and SH-3 was replaced shortly after by SH-56. In 1931, SH-48 was greatly expanded. The route was extended northward to
US-66 in Stroud. At its southern end, it was extended along a new alignment, which began at
SH-19, present day SH-3, southeast of Ada and ran through Tishomingo and Madill to end at the Red River northwest of
Denison, Texas, where it met
Texas State Highway 91. Also that year, a second section of SH-48 was established, taking over a large portion of what was then SH-25; the remainder of the route was integrated into US-60.
Renumbering and realignments On May 17, 1938, both Kansas and Oklahoma renumbered K-11 and OK-48 respectively to bear the number 99, providing continuity between the states. At this time, SH-99 followed the same basic corridor of the present-day route from Madill north to Kansas. However, SH-48's designation was still in use from May 1938 to February 1941. The SH-48 designation was then made into the route passing through Konawa, which the SH-99 designation bypassed. After SH-48 was discontinued, however, it would only remain discussed for just under three years, SH-48 resurfacing for a route only east of SH-99. On May 5, 1958, the route was realigned to once again reach Texas; which was subsequently renumbered to Texas State Highway 99. The existing route of SH-99 (concurrent with SH-3) veered west by about to once again serve the town of
Konawa before cutting back northeast to continue the highway's previous heading. This was remedied on December 9, 1968, when the highway was changed to a straighter alignment bypassing Konawa. The old road heading west into Konawa became part of SH-39. all of which were rejected for unknown reasons. In 1988, ODOT began signing US 377 from Madill to Stroud along SH-99 without AASHTO approval. ==Spurs==