Our basic idea of warfare in ancient India is flawed. When we think of a battle between two “Maharathis” we tend to think like this : 
or this : 
But we fail to understand, that two great warriors will never face each other one-to-one like this without their soldiers or guards. There are battle plans, soldier formations & tactics of both. Comparing from this perspective, Bhisma was the commander of the Kaurava army, which was respected & feared all throughout the country. His strategies both on & off the battlefield, forced Emperor Jarasandha (who ruled over a bigger land) to refrain from open war against Hastinapur. The arch-rivals of Hastinapur, the Panchals, once demanded their throne during political turmoil in the Kaurava kingdom & asked them to hand over the queen, Satyavati to them. Bhisma responded by killing the Panchala king in open battle. The Pitamaha of Hastinapur was well adept in both “shastra” (knowledge) & “shostra” (weaponry). He marksmanship & anti-weaponry (knowledge of which weapon to use against which) was legendary. Even Parashurama failed to defeat him. 
On the other hand, Karna, whose real name was Brishasena, was a skilled warrior & a great archer, no doubt. He was considered equal to Arjuna (although never proved). In fact, he was hailed more by Duryodhana as an answer to Arjuna & made king of Anga. As per his armour, it was a good story !  We tend to be partial towards Karna, more because of his misery & good nature, than his prowess. 
Hence in my opinion, Karna doesn’t stand a chance against Bhisma. 
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