Fictional dogfight.
Plane A : USA made 1941 Brewster Buffalo ever deployed stationed in Singapore in the past. Armed with machine guns.
Pilot A: Best pilot of top gun school. Pilot skills ranking 95 out of 100.
Plane B : USA made F15 - Eagle armed with missiles and gun.
Pilot B: Worst pilot of top gun school. Pilot skills ranking 50 out of 100.
Weapons System Officer B: Worst of his class. Skills ranking 50 out of 100.
According to the theory that it is the man behind the equipment and not the equipment, Pilot A should win the dogfight.
You didn't state the conditions, time & terrain of the fight. Hence I'll rule in favour of the Pilot A since he being more skilled will know how to milk every opportunity to his advantage.
1. Mid day sun. Day time when it's the hottest, and to negate enemy from hiding in the sun.
2. over Jungle. Heat reflected off the jungle to negate IR missile lock.
3. Mountainous terrain. Have ridges and canyons to hide in or break radar/missile lock.
4. Clear sky. No clouds to hide in.
Tactics:
1. Stay low. Employ Nap of Earth flying to minimise radar lock and hide from opponent.
2. Stay slow. The only real advantage, which will cause opponent to overshoot or slow down enough to get a shot off.
Pilot A has little to no chance of actually claiming a kill on Pilot B, and an overall low chance of getting out alive. His best and only hopeful outcome is by continuing to frustrate his opponent and cause him to leave (bingo fuel/weapons). This looks like a draw but actually a win for P.A and lose for P.B.
Unless Pilot B is really so dumb as to fight in Pilot A's rules, then he may make the mistake of either gifting a free shot or ramming himself into the terrain so P.A will win the fight by default.
