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Just keep working at it. You say that will go into it, but pulls out. So, the question is ‘Why is he pulling out?". The answers to that are 1) he does not have the strength to hold that headset for long periods; 2) you are ‘dropping’ him (breaking contact by either loosening the rein or lightening your leg and seat; 3) you are stiffening up and he is taking his head back from you because it is painful for him.

Since you have a show next weekend, would it be possible for you to find someone who is a professional who can ride him and assess whether he has the muscle for the job, or if it is a rider issue?

Either way, be patient and keep working. Dressage judges understand that horses and riders are works in progress, and you will probably be given some excellent professional advice from him/her regarding your training and level!

Enjoy the show, work toward it, and just do the best that you and your horse can do at this time. Take the judge’s comments and consider them in the training that you continue to do.

It’s because he’s weak in his topline, so once he gets in a nice frame, it gets difficult so he quits. Also, you’re probably focusing on his headset when what really matters is what he’s doing with his haunches and hind end in general. You may also have inconsistant rein lengths. Do your reins seem longer then shorter? that can cause lots of head tossing.

Remember to overpower your rein aids with your leg and weight. I learned that in a lesson today, my horse would toss his head, but what it turned out to be was, I wasn’t being strong in my hands to the point where I was reefing on his face, but I was using more rein than leg and weight, which made him angry. Right when I used more leg and seat, he kept his neck level. it was great! So keep that in mind.

I’m glad you aren’t just blaming the horse and giving up on him, its refreshing to see someone recognize that humans make errors too.
Do you have an instructor that could help? Remember to do lots of half halts with your seat and leg, and supple his jaw by "vibrating" your ring finger on the reins.

"Success lies in the giving rein"

This is hard to answer without seeing what is going on–I am going off you saying that he is "pulling out of it" which makes me think of 2 things it could be. This description makes me think that he is leaning onto the bit.

1. As a TB, on the track he learned to balance off the bit, these first experiences are really ingrained into OTTB’s and they will frequently revert back to it if you aren’t careful about their balance. Perhaps you aren’t getting him balanced enough so he is going to what he knows–balancing on the bit. Lots of transitions and half halts will help him to rebalance onto his hind and get into frame. Ride from your inside leg to your outside hand, driving him into your outside rein.

2. He is seeking contact but you aren’t taking it, possibly mistaking the correct feel for dressage based on other types of riding you have done. The feeling of contact might seem wrong to riders who come from breed circuits or western riding, who are used to a draped rein and little to no feel with the bit. Contact should feel elastic, where your reins aren’t super taught, but aren’t flapping around either–contact is just what it sounds like, you should have contact with your horse’s mouth. An elastic feeling–where if you imagine a tissue connected between the bit and your rein, your feel is just enough to keep the tissue taught but not break it. When the horse seeks contact, you add a bit of leg and give and there you go–the horse is on the bit.

Remember, the headset is the product of proper carriage, you don’t work on the headset, you work on the body carriage and the headset happens.

First have your saddle, bridle and bit fit checked. Some horses rush to avoid a pinching saddle, bridle, or poorly fitting bit. You don’t say what type of bit he is in. My personal favorite is the JP curve french link eggbutt snaffle. The gold one was the best, but korsteel doesn’t make them in that alloy anymore (which is a complete shame!). If he is in a single joint, loose ring, or a poorly constructed french link (one that is fairly straight), it wouldn’t hurt anything to switch to this bit. It is very good for training, fits the horse’s mouth nicely, and is one of the most mild bits you can use. If it isn’t a tack issue, continue on:

Focus on riding from back to front, inside leg to outside hand. He’s a TB so he gets fast isn’t why he gets fast. Plenty of horses that aren’t OTTB’s get fast too. He gets fast because he is heavy on the forehand. By pushing him forward and in front of your leg he will slow down. I know, it seems odd that the way you are going to make him slow down is using more leg, but it is what you will have to do. You and your horse need to learn that the leg also means sideways and deeper.

A good exercise for this would be to practice riding your corners. Set up some poles so that you have a box in the arena that is 66′x66′ (if you are riding in a dressage ring you would block off one end of the dressage arena so you are just riding in a square, 66′=20m). Then rather than riding a 20 m circle inside your box you will ride as deep as you can into each corner. The corners are the best place to ride into, rebalance your horse, and give an optimum half halt. A half halt doesn’t necessarily have to be on both reins with both legs. For your horse, the best half halt would be with the inside leg and then on the inside rein, so that he is going forward in shoulder fore. He won’t be perfectly straight, no, but it will keep him from rushing through. As you practice your corners (and shoulder fore) focus on your outside rein remaining perfectly steady and push your horse forward into it with your inside calf. Always push push push, especially if he is rushing. Your inside rein will do the half halt. If he crosses his jaw, then you will ask him to counter bend (outside leg to inside hand) but it is very unlikely you will need to do this. By doing this, you are asking him to pick up his back and step further under it with his inside leg. He will probably rush more at first, just focus on riding him forward even if he rushes rather than slowing him down with your reins. Spiral in and out is also another useful exercise to practice. Practice shoulder fore and shoulder in on a circle.

I think in your situation the most likely situation is that he is in tack that doesn’t fit properly or tack that doesn’t fit you properly and makes it so that you can’t use your leg well. If the tack does fit the two of you, then you aren’t using the leg right. If you stand straight up in your stirrups and find the spot you can balance without falling down, when you sit back into the saddle your lower leg shouldn’t move forward from that place. If you see pictures of upper level riders you can see just how far back your lower leg should be under you. Once your leg is on the place the horse is wider, then your leg is more effective. You might be riding with it too far forward in an attempt to keep him slower, so work on bringing it back and under so you can use it better.

Good luck at your show next week!

Others have hinted at it, but I’m going to give it to you straight: anybody who focuses on the "dressage headset" has a serious hole in their education. A big hole. One large enough to drive a truck through.

Truly I’m not trying to be mean. I like your attitude. You don’t blame your horse, you want to know what you are doing wrong. But the headset is not something you should ask for. It is a result of getting your horse to engage his hindquarters and lift his back. Most of us are under the impression that flexion comes from the neck, poll, and jaw, but it is actually engaged by the horse’s ring of muscles, which are activated by the rider’s driving (leg) aids. Yes, he has to release tension in his jaw and poll, which is why you sometimes need to use a soft "give and take" or "sponging" on the inside rein. But it is not the reins that produce that beautiful headset. It is your legs and seat engaging your horse’s hindquarters that counts, while your reins simply contain and shape that energy from behind, recycling it back of the horse’s back to his hindquarters again.

So go back to your instructor and keep taking lessons. I suspect you wanted a quick fix (like: try this bit! OR do such-and-such with your reins when he pulls out) but that’s not gonna happen. Sorry, it will take time and work.