Why is it odd?
From your own figures the Nissan made more HP up to about 9,000 ft. By then the Nissan was so far ahead that they beat the oil burner up the hill.
It would be informative to learn what Cummins would have to say about the test. By way of information the testers state the Ike grade is an almost constant seven percent, perhaps the steepest grade for eight miles of any interstate route. Also, the Ike gauntlet tops out at 11,100 feet and the test begins at around 9000 feet. So, the gasser would be down close to twenty percent of it's sea level power. The Cummins should make almost sea level power at 11,000 feet since it is turbocharged.
The Titan Cummins is rated at 310 hp and 555 foot pounds torque, basically all power is available up to the summit/tunnel. The Titan's Endurance gasser is normally aspired and comes with 390 hp and 401 foot pounds torque. At 9000 feet, the start of the test, the gasser has lost almost twenty percent of it's sea level power so it would start the test at 311 hp and 327 foot pounds and at 11,000 feet the numbers would be 27.5 percent lower than sea level; or 280 hp and 296 foot pounds torque. The seven hp needed for the additional 1000 pounds the diesel towed should not have made that much of a difference.
The difference must be in the rear end ratios or the transmissions. Just watching the test it would be hard to spend the extra money for the diesel (unless you just love diesels) as it's performance was not that spectacular and it only got about twenty percent per gallon better on the wide open throttle climb.