Make sure you have 1 or more strong mercenaries with good health in your squad, ideally with high experience levels and a specialty in hand to hand or martial arts (Bull, Grizzly, Dr. Q, etc.). Although Darren van Haussen the club manager will advertise the Extreme Fighting competition as purely bare knuckles (no weapons of any kind allowed), there is however some room to get an edge in each match. For some reason the mercenary that enters the ring is allowed to wear armor and equip knuckle dusters. Using other weapons or letting another mercenary enter the ring forfeits the match.

When you talk to Darren for the first time he will explain the rules and says that he will accept any amount of money between $1.000 and $5.000. He has 3 fighters, but if it´s the first time partaking you sadly can´t bet $5.000 per match to make a profit (a bug perhaps?). This means that if you go all-in on the first match and win, Darren will hand you over $10.000 (your own money plus his $5.000 which is all that he has the first time). After this you are basically at best paying Darren to kick the ♥♥♥♥ out his other 2 fighters or even worse, getting you ass handed to you.

It is however important that you win all 3 matches the first time, because this will impress Peter Klaus aka Kingpin. Kingpin is the mayor of San Mona and a fan of the bloodsport. He is also the club owner and a businessman that sure knows how to spot a good opportunity when it presents itself. He will invite you over to his manor to discus his plan for obtaining a specific item to add to his collection of valuable items and making you filthy rich. This will trigger a quest for the Chalice of Chance.

Spread out $5.000 over 3 matches, for example: $1.500 + $1.500 + $2.000 or $3.000 + $1.000 + $1.000. Luckily you´ll only have to do this once. In future matches you can max out your bets at $5.000 per match and receive $15.000 in winnings.

Have one mercenary face Darren. Place your fighting mercenaries close to and around the ring to preserve their stamina. If you have put everybody in position fast forward the time 5 minutes and pause to refill the stamina bar of your fighters.


Save the game.

Let the mercenary facing Darren do the talking and click yes to fight his guys. This mercenary will also handle the cash to prevent a bug from happening wherein you won´t receive your winnings. Withdraw the amount of cash you want to bet and give it to Darren to get the match underway. The doorman will inform Kingpin, since he wants to attend every Extreme Fighting competition.

Let your fighting mercenary enter the ring and win the match. Darren will hand over the winnings to the mercenary facing him and asks if you care for another, click yes. Deposit your winnings into your bank account and withdraw the max betting amount again. Optionally have a doctor in your squad to patch up your fighting mercenary if he took some punches. Do the same for the final match.

If for some reason you lose a match. Load the earlier saved game to start over.

Don´t immediately start the Extreme Fighting competition again after you´ve won (or lost some of) the 3 matches. If you do this Darren´s fighters won´t enter the ring and there are no refunds. Instead, wait at least 2 days before you can partake again.

It may sound crazy but optionally your doctor can patch up Darren´s fighters for their health recovery. Why the ♥♥♥♥ do you want to do this? Well, it´s your best interest to keep the geese that lay the golden eggs alive. Even after you´ve waited for 2 days and Darren´s fighters are supposed to be fighting fit again, you´ll see that they are in poor health. So it´s not something that you do out of the kindness of your heart, but purely because of business reasons.

If Darren´s fighters are in poor health, your strong fighting mercenary will certainly beat him to dead or leave him dying. If 1 or all 3 of Darren´s fighters die, they won´t be replaced. It is key that they stay healthy.

There are 2 things you can do about this:

1. Wait a little longer so they recovered some more
   
2. have some of your weaker mercenaries fight them and they will receive experience in the progress

Don´t forget that the Extreme Fighting competition is just business, not killing off enemies. If one of them dies it will negatively affect your bottom line and you want to max out the ROI.