WWE 2K19

If need be, switch the difficulty to Easy.
Easy Difficulty can be found in the Main Menu, by scrolling to Options & selecting Gameplay.

Start a Steel Cage Match with AJ Styles VS Curt Hawkins. Play as AJ.
His Minor Payback Ability, "Instant Recovery", will make this much easier.

Beat Curt up to the point where his health is red, or lower. Now, let him beat you up, to the point where he has his Signature Move. By now, you should have AJ's Recovery Ability. If Curt uses his Signature Move on you, don't panic. This usually means that he will start climbing up the cage. Once Curt starts the first minigame to make it further up the cage, use that Recovery ability, & climb after him. You should have a lot of time to make it to the top. If he does make it to the top of the cage, again, don't panic. He has one more minigame to complete before he slides to the other side & wins the match. Once the both of you are at the top & straddling the cage, punch & grapple Curt until AJ throws him all the way back down to the mat.

Achievement Unlocked.

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If you have a way to make this even easier, feel free to share it in the comments below.
Once someone else confirms it, I will add it to this solution.

Happy Halloween, you all.

There’s an easy way to kill three birds with one stone and get the “It’s a long way down” and “Over but not out” achievements as well as this one within literally five seconds of each other.

-Pick AJ Styles and wrestle Curt Hawkins in a Steel Cage.

- (1st Achievement - Cage Top Drop) Throw him off the top of the cage by just grappling him up there when you’re both straddling it. That gets you the first achievement.

- (2nd Achievement - It’s a long way down) Then just press X to hit him from the top of the cage and you get this second one right away.

- (3rd Achievement - Over but not out) Now pick him up and hold RB and UP on the Right Joystick to carry him. Approach the ropes while carrying him and hold RB and then X to slam him into the side of the cage. That’s your third achievement.

I was gonna say you can get this by having instant recover activated against Curt Hawkins, hit him with your finisher, climb the cage and let him pull you off.

However, when I was going for the achievement, I heard "Say yeah!" and Dash Wilder came out. So I punched him a few times before throwing him off the top of the cage to the floor and got the achievement.