Grand Theft Auto IV

You have to win on 20 different tracks in ranked "race" mode. I found Boat and Helicopter races to be the easiest because most people can't drive the boat/helicopter very well. Take a little time to learn how to drive them and learn the tracks, and you'll have a good chance of winning those races. The rest will have to be won with cars or bikes. Again, learn the tracks and know where to brake for corners. Eventually you'll improve and be able to win the occasional race.

NOTE #1: There must be at least two players remaining in the game for it to count as a win. If you ever see the screen saying "last player remaining", that race will not count as a win for you.
NOTE #2: GTA Race does not count for this achievement.
NOTE #3: Player matches do not count for this achievement.

In addition to what's been said already - if you check on the ranked leaderboards you can see how many times (if any) you've won each race.

Make a note of which you haven't won yet so that on the odd occasion that you do get control of the room you can put it on one of those races (assuming you don't get majority booted when people realise you've chosen a boat-race!)

Good Luck.

EDIT: The ranked leaderboards I refer to above are on the Rockstar Social Club website, not in-game, & can be reached here... http://socialclub.rockstargames.com/

For this achievement, you have to win 20 different races in ranked race mode. If you are doing this on the way to getting the Petrovic achievement, you should record which races you won. Please note that:

1-You have to win on 20 different tracks
2-GTA Race wins don't count towards this achievement.
3-Player matches don't count towards this achievement.
4-There has to be at least one person left until the end of the race. If ever a race stops because you are the "last person remaining", it will not count towards your 20 wins.
5-You can check if you've won a certain race by going to the leaderboards and then selecting "Mine" on the view scores page.

I got this achievement on my way to getting the Petrovic achievement, so I boosted most of the races. You've probably seen tips to do races legitly, so I'm going to try and help you guys by giving you some 2 player boosting tips:

-If you or/and your partner are in a lobby with a lot of people, wait till the race starts and then quit out at the starting line using your phone
-If you're ever in a lobby with one other person, try and scare them off by putting the worst settings possible. Ex: Laps - 8, Time of Day - Midnight, etc.
-If you and your boosting partner/s are in a lobby with a decent amount of people and you need one or two gone before being able to kick everyone out, go for the host or Rank 0's.

You should eventually get matched up and will be able to boost the races. Happy gaming!

Goal: Win 20 Matches in Ranked--> "Race"

As other solutions have mentioned:
- you can check your number of wins on the rockstar website
- MUST be in 'Race' not 'GTA Race'
- Single Player/Player Matches do not count
- You must win on 20 DIFFERENT TRACKS

Basically all I am about to say it is a method to attempt to get you into a lobby with only a few other players, thereby increasing your chances of winning. This method does not guarantee that you will win, or even do good, it just tries to improve the odds of you becoming host.

What I am going to say works for me, and my router, I am by no means an expert on how all of this works so I don't know how repeatable it will be for you.

Basically, we will set our router's NAT type to be 'Strict' -- Which limits our ability to connect to other players, and in the case of GTA4, this causes you to be assigned host very often, and not as many other players will be able to connect to you.

I found all this out by accident when playing on a NAT:Strict connection, that was not at my house where i normally play. some games will tell you something to the effect of "your NAT type is set to strict - this may limit your ability to connect to other players or find matches" (red faction does this, a few others...) Anyway, you may see a down side to it - you wont be able to party chat some of your fiends ("cant connect to party") unless someone else you can connect to is also in the party (and if they leave you both will get disconnected)... like I said, I am not sure how all this works, these are just my observations.

So after you change your NAT type, go search for a match... you are likely to be disconnected a few times before you find one, or it assigns you host. Once you are host, set whatever vehicle/map combo you prefer (my favorite is police vehicles, with the FIB(lol) Buffalo being the best) Set your settings, ready up, wait for someone to connect, and hope they ready up before too many others join (usually not that hard...)

Unfortunately, you may find a lot of people who will quit early when they realize they are going to lose a 1v1. If all of your opponents quit, the match DOES NOT COUNT AS A WIN :(.

Good Luck, i got this achievement in approx 5 hours of strait playing (0 wins to 20 wins). During that time i had 8 people quit out on me, as well as a hand full of people who screwed me up by driving backwards (in 3 person or more matches).

You may keep getting disconnected and returned to single player, or disconnected from a lobby and offered to start a new one of your own, but keep at it and you will get it much faster than hoping to win against 10+ other lunatic drivers.

(PS this method also works Join the Midnight Club - Win a match without damaging your vehicle - I suggest using helicopters - as they are hard to damage...)

When you are done getting this achievement, simply change your NAT back to Open or Limited - whatever you had it at before you originally changed it.

For Instructions on how to change your NAT type, I suggest Google-ing your router brand and 'how to change NAT'

I, like most people, got this Achievement whilst going for Auf Wiedersehen Petrovic. It is easiest done on the Road, Boat and Helicopter race classes, as not many people like the Free Races and Cannonball Runs, so don't quit the session. The best way to do this is by being the host, so you can select the track you want.

For Road races, I've found that having Trucks, more specifically, the Fire Truck will help massively, as I have found out that when you fire water out of the hose (LB), you appear to go slightly faster than the other players due to a lack of friction (or a glitch). This means you get them done a lot quicker.

For Boat races, the Jetmax and Tropic are the fastest boats, and have the same stats for everything, but I personally prefer the Jetmax. To win, you want to press LT almost constantly, and hold RB whilst taking corners. You also want to avoid crashes with other racers, and don't miss checkpoints as it takes a long time to get back to one.

In Helicopter races, the Annihilator is the fastest. You want to keep on roughly the same level as the next checkpoint you're aiming for, not too high, not too low, and press the analogue stick forward to get to top speed. Also, don't crash into any other racers, as this will cause you to spin out of control, and you may lose your rotors. The same applies to hitting buildings.

These are generally best done with at least two other friends, assuming you're trying to boost, so that the other two can help kick other players. If you're doing it solo, then it should be possible to win, but slightly harder.

The easiest way of doing this is to boost - find a partner who has a mic and take it in turns to create a ranked standard race lobby - kick all randoms and set to one lap races, clear weather and no traffic. Make sure to mark off each track once you've each completed. This takes a while as the match making system is terrible, you'll need roughly 3/4 hours to do this - definitely do-able.