No, you don't have to list the individual transactions; however, you do have to report all your gambling income.

Gambling losses are only allowed up to the amount of your gambling winnings. For example, if you had $9,000 of gambling losses and had $2,000 of gambling winnings, you can only deduct $2,000 of your losses (the amount of your winnings).  If you had no winnings, you will not be able to deduct your losses.

Normally gambling winnings are reported on form W-2G.  However you can enter your gambling or prize winnings in TurboTax (even if you didn't receive a W-2G) by following these steps:

1. Click on Federal > Wages & Income   
2. In the Less Common Income section , click on the Start/Update box next to gambling winnings.  
3. On the Gambling Winnings screen, click the Yes box.
4. On the screen, Tell Us About Your Winnings, click the Skip W2-G box if Form W2g is not issued.  
5. On the next screen, Any Other Gambling Winnings, click the Yes box.  
6. You will be able to enter your winnings in the Other Gambling Winnings screen. 
7. Since gambling losses can be deducted as an itemized deduction (up to the total of reported gambling and prize winnings) enter your losses (if any) on the next screen, Gambling Losses.  

[Edited | 3/18/2020 |  1:10 pm PDT]