Updated September 2026
Best Owner-Operator Companies in Stillwater, Oklahoma (September 2026)
Stillwater, Oklahoma, September 2026: 599 active owner-operator carriers. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. Oklahoma freight is shaped by the I-35 / I-40 cross at Oklahoma City — a major north-south and east-west junction — with energy-sector service loads in the Anadarko and Arkoma basins and agricultural freight from wheat and cattle production.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where owner-operator pay is strongest in Stillwater, Oklahoma this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC leads the Stillwater, Oklahoma market on combined gross revenue and ranking score this month. The carrier ranks in the 94th percentile for gross weekly revenue in Stillwater, Oklahoma. RAY'S TRANSPORT INC ranks in the 87th percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Stillwater, Oklahoma median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Driver applications get a faster-than-median response in Stillwater, Oklahoma.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,500/wk, #5 WIDER GROUP INC at $6,250/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 C & G TRANSPORTATION INC at $7,500/wk, #8 AIA TRUCKING INC at $3,450/wk, #9 M&D TRANSPORT at $7,000/wk, #10 JK MOVING & STORAGE INC at $4,975/wk.
What Stillwater, Oklahoma drivers actually run
8% of Stillwater, Oklahoma's active CDL postings are regional and 92% are OTR; local plus semi-local accounts for the rest (0%).
Guaranteed pay is on offer at 2% of Stillwater, Oklahoma postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 73% and riders-allowed at 71%.
How Stillwater, Oklahoma compares to Oklahoma
Among the figures above, average weekly pay is where Stillwater, Oklahoma differs most from Oklahoma — 4% above statewide.
Driving CDL in Oklahoma
Oklahoma freight is shaped by the I-35 / I-40 cross at Oklahoma City — a major north-south and east-west junction with substantial through-traffic. Energy-sector service loads from the Anadarko and Arkoma basins add oil-and-gas equipment freight, especially in active drilling cycles. Agricultural freight (wheat, cattle, cotton) is steady outbound. Tornado season (April-June) shapes spring dispatch across the state — route planners watch the outlooks. Oklahoma has a low graduated state income tax; housing and operating costs are among the lowest in any major US state.
Related guides
- Best trucking companies in Stillwater, Oklahoma
- CDL driver salary in Stillwater, Oklahoma
- Best owner-operator companies in Oklahoma
How we compile these rankings
Composite-score formula: compensation × 0.30, FMCSA safety × 0.25, benefits × 0.25, operational performance × 0.20. Compensation is anchored on pay percentile and lifted by sign-on bonus tier and guaranteed-pay availability. Operational performance is built mostly from driver-application response data in Lanefinder's platform, with fleet-scale percentile contributing a smaller portion. Updated September 2026.