I'll try to keep it short and simple..

At a house party things got out of hand, I was in a rush to leave and while reversing scratched a car that was parked next to me (parked there after me and there were cars squeezed in on the driveway everywhere so nobody gets ticket on the street).

I told the person I'll cover the damage, few days later he tells me the price, shop where he'll go etc and I bring him cash and have him sign a document stating that by accepting the money he agrees that covers any and all damages done to his vehicle that night, it states what will be repaired and that I will be getting receipt for the repairs performed in 10 business days. He signed it.

Then later he says sorry no receipt, of course since damage was so small it can be buffed out so his plan is probably to pocked the cash. Well it's matter of principle now so I want the receipt and I'll go to small claims court to enforce this in needed.. get a lawyer too (even though it'll cost me, again, principle).

Any thoughts?

He deserves the money, he is not required to get it fix, merely give you an estimate ( you may ask for 2 or 3 to be sure the first estimate is not too high)

If he sued you for the money he would have won and was not required to provide proof it was fixed.

Just be glad it was done and forget it.

When you damage a persons car you are required to "make them whole." That means you pay for the repair or the cost of a repair but the owner can decide to not repair the car and keep the cash. If this were a larger damage, reported to your insurance your company would write him a check made out to him. He could cash that check and use it for repair or anything else he cared to buy.

Damage was done on private property, not city property, he agreed to provide the receipt to me for tax purposes

You did the right thing in getting him to sign a release. But you can't enforce that he's required to show a receipt for the repairs. You can't even require him to make the repairs. So save your time and money, you will lose in court

Matters not, your canceled check can be your receipt. Tax purposes? How would a payment for car damage have a tax implication?

Happened to me once before, that time I was not at fault, but also private property. According to the insurance that means 50/50 liability.. so in this case in order to calm things down and forget it I paid, but I also requested receipt on a document which this person signed

It was cash payment releasing me from any and all future claims but also agreeing to provide receipt, so he agreed and signed that.

Issue here, and reason I asked for receipt, is to make sure damage caused actually costs that much to repair

You didn't ask to see the estimate? That was your mistake.You apparently felt the amount was reasonable. You are still highly unlikely to win.

A few issues:

First mistake was not requiring him to get a written estimate.

You paid cash and expected a receipt. That was your second mistake. You should have paid by check. In any event, as Ballengerb1 suggested, it is doubtful that you need such a receipt "for tax purposes" anyway (Yes, I realize you are in Canada, but still.)

The document signed states that this is I no way admission of fault, I just felt bad for the guy since he had some damage and I didn't.. basically it's a signed contract of me giving him money to repair his vehicle, stating what will be repaired, and that receipt will be provided to me, so what I'm looking is to enforce contract he signed.

He signed he got the cash, signed it is to repair a vehicle, and for what repairs, and that receipt will be provided to me.

Thanks for all the answers

Do you both have copies with both your signatures? How much money did you give him?

He didn't even ask for a copy so I have the original and it was $400

What you don't seem to want to understand is that you can't require him to prove he made the repair. Therefore, that part of the waiver is unenforceable.

I understand that point if this was admission of guilt/way to avoid insurance, but it is not.. whole contract is me giving him money to make a repair to his vehicle and provide me receipt

Sorry, but you are wrong. You damaged his property, you are responsible for compensating him for the damage. What he does with the compensation is his business and you can't force him to actually make the repair. Which means that you can't enforce that part of the waiver. And no this was not a contract. It was a waiver of any future liability on your part.

Even though he agreed/signed he will be providing me the receipt?

Again, that part of the waiver is UNENFORCEABLE!

You go into court, the judge asks if you damaged his car. He asks if you felt the amount he asked for was fair and if you willingly paid it. You answer yes, yes and yes. He says goodbye.