This could be one of the most difficult and/or frustrating missions in Grand Theft Auto: Vice City. Hilary's car appears to be faster than Tommy's Sentinel; but in fact, he can only accelerate faster and corner slightly better than Tommy. In a straight-a-way Tommy will be able to pass him.
Two strategies for completing this missing:
1. When Hilary is turning or weaving, try to tip the rear end of his car and put him into a spin.
2. If the player passes him and gets far enough ahead of him, an oncoming police vehicle will ram him (due to the preprogrammed way the cop cars make u-turns to come after Tommy).
Regardless, one has to run a nearly perfect race to win it. Beware if Hilary is right on Tommy's tail; he'll try to point-and-turn Tommy.
- If Tommy starts this mission with a sniper rifle equipped, after the 3-2-1 countdown jump Tommy out of the car and quickly lock on to a tire on Hilary's car and blow it. Though Hillary will gain a sizable lead, with a flat tire Tommy easily pass him and cruise to a win.