ONRUSH

You will get CHECKMATE! medals, if you wreck enemy vehicles into obstacles i.e. wall, pillar, etc. In-game it's described as "CHECKED OUT! takedowns - Shunting an enemy into an obstacle. You can also get 50 bronze medals for this achievement - counts only for enemy takedowns, Fodder cars/bikes don't count wowards this medal!

Note, that you can also earn medals in Custom Game via Play in the Main Menu. There you can shorten the races and tweak difficulty and other things.

You will need to get a minimum of 2 CHECKED OUT takedowns to get a bronze medal (thanks for pointing out illdizzog ) for it to count towards the progress in the achievement tracker.

I would suggest to just keep playing the Career events and then get the rest of the medals, if you need any, via Custom Games.

CHECKMATE! medals are awarded for bumping (shunting) opposing team vehicles into obstacles such as trees, walls, etc. resulting in a CHECKED OUT! notification. This is harder than it sounds because often the enemy will wreck some other way (such as TAKEDOWN!) or you'll mistime the hit or even wreck yourself.

Quick Rundown
- Shunt opponents into obstacles to trigger the CHECKED OUT! notification.
- 2x CHECKED OUT! takedowns = 1 bronze CHECKMATE! medal.
- Only 1 bronze medal can be earned per game.
- Achievement progress is updated immediately after earning the medal in-game, meaning quitting and restarting to speed up the process is recommended.
- Fodder does not count.
- Use the Achievement overlay to keep track of Eat DiRT during gameplay to ensure you earned the medal before you quit/restart.

This achievement is best left for last to minimise grinding, but if you have to grind some out like I did (I had to knock out about 12 medals) then below is what worked best for me. From the main menu, go to Play > Custom Game and try the following setup and strategy:

Custom Game Setup

-- Environment
TRACK: Freightyard Forest
START TIME: Midday
(leave the rest as default)

-- Gameplay
MODE: Countdown
EVENT LENGTH: Extra Long
DIFFICULTY: Very Easy
VEHICLE RESTRICTIONS: Cross out everything other than Charger for both teams. I found this car has the least disruptive Rush and being the same size reduces the chance of wrecking the enemy in a way other than checkmate.
(leave the rest as default and start the game)

Strategy
- When the round starts, hang behind the group of enemy cars, staying alive until they reach the train yard. The countdown gates make their movements somewhat predictable.
- On approach to the train yard, boost into the centre of the group.
- Now in the train yard, swerve left an right to shunt them into anything around you!
- Once you see the bronze CHECKMATE! medal pop up or the progress for Eat DiRT move up a notch on your achievement overlay, press , Quit, and repeat.

Most likely this will be one of your last achievements that you'll need. The easiest way to do this is to just start up a custom game put the AI on easy and go the map with the trains. For a checkmate to count you have to do 2 of them in one game, And you can only do one or these per match. So once you get 2 just quit the game and start it back up and rinse and repeat. By time youre done with the challenges this should only take 10-15 min I was at 92% and this was the last achievement I needed.

TLDR: Play= Custom Game. Event= Count Down. Race Length= Very Long. AI= Very Easy. Track= Jedhora. Vehicles turned off= Vortex and Titan. Vehicle used= Dynamo.

As the other solutions have stated, a Checkmate bronze medal is awarded for two “Checked Out” takedowns in one race event. Getting more than two Checked Out takedowns in one event WILL NOT earn additional Checkmate bronze medals. I tried using the aforementioned methods/solutions, and while useful and valid, they weren’t working for me. Here’s what did work for me:

As the other guides have stated:
Custom Game is a great way to farm this. Count Down race event is good. Set the AI to Very Easy and the race length to Very Long.

Here’s what I did differently:
The track Jedhora worked best for me. The cars I turned off were the Vortex and the Titan. The vehicle I used was Dynamo.

Here’s reasons:
Checked Out takedown is achieved when you push/ram/bump/steer/or otherwise cajole an opponent into a track obstacle, wall, or off the edge. You bump the opponent car and if this causes it to get the exclamation point above it (which means it’s in danger), and then it smashes into something or off the edge, WITHOUT hitting one of your teammates, you’ll get a Checked Out takedown. IMPORTANT! Some vehicle’s boost power will change the nature of the takedown! Example: The vehicle “Interceptor,” will change many takedowns that would’ve counted as Checked Out into Power Surge, because of its boost power.

Jedhora track is perfect because it’s fairly narrow most of the time. This means you’ll be close to your opponents and they’ll be close to the walls and/or the edge of the track. Use this to your advantage and bump them as much as you can. There are lots of narrow choke points where you’ll be driving across bridges and/or through archways. Bump opponents as you approach the openings or force them towards the edges. Even if you crash in the attempt, it is still possible to earn Checked Out takedowns. I got several posthumous Checked Out takedowns (which popped up after I respawned back into the race) on my way to earning this achievement. Also, there are several sweeping turns with no edge walls. Bumping opponents off these edges also earns Checked Out.

Count Down mode is good because during the first period you can focus on hitting gates while also trying for the occasional Checked Out takedown. During the second period, I’d suggest intentionally missing gates, thereby increasing the chances that your team will lose that period, thus forcing a third period. This gives you more time/chances to earn those Checked Out takedowns.

I suggest leaving most vehicles turned on. This gives you a wider variety of weaknesses to exploit. Trucks are big targets and very vulnerable to choke points. Buggies and bikes are easy to push around if you can hit them. Cars are easier to hit than bikes and buggies, but harder to affect. Turn off Vortex as it’s Rush ability can really affect your driving and the paths you can take. I also turned of Titan to prevent it shielding its teammates.

I used Dynamo. The cars have a better balance of size and speed, and Dynamo’s boost won’t affect getting Checked Out takedowns. Interceptor’s boost does change the takedown most of the time. Yes, you can get Checked Out takedowns with Interceptor, but if you’re boosting, quite often you’ll get Power Surge takedowns instead.

Side notes/tips:
Avoid smashing into vehicles too hard!!! You don’t want to smash the vehicle itself! You want the vehicle to smash into something else... like a rock or a wall, or off a cliff. You just want that happening to be your fault.

If you fall too far behind, don’t bother trying to catch up. Just crash, or hold the window pane button on the controller to reset yourself. Trying to catch back up usually takes too long, and you have to get at least two Checked Out takedowns before the end of the event. If you run out of targets, use right stick to look around. If you’re too far ahead, hit the brakes and let them catch up.

Don’t worry about winning the event. Focus on Checked Out takedowns. If you can win along the way, that’s great, but we’re going for Checked Out takedowns, and that Checkmate bronze medal, not wins. You still earn Checkmate bronze medal even if your team looses the event.

Lastly, and perhaps most strangely, I remapped Boost to Left Trigger. I realize this change just won’t work for a lot of people, but it helped me. This freed up my right thumb to use the right stick to look around, find targets, and position myself to attack, while still boosting with LT. I remapped brakes to A button. I find I don’t use brakes much in this game anyway. It takes some getting used to, and I find that in a panic I still mash LT when going for the brakes, but mostly it was a helpful change for me. I would’ve remapped Boost to Left Bumper, but the game won’t let you because that’s the “match stats” button.

Hope this helps. Good luck.