Every Monday

8 am - 10 pm

More Winners! More Payouts! For all guests 50+! The participants will be eligible for 5x the entries for the $3,000 Travel Voucher Drawing on April 29, special $5 Silks Bar and Grill menu and more! 

For the Monday Funday menu, click here.


  • Silks Discounts: From 11 a.m.-10 p.m. guests aged 50+ qualify for a special $5 menu in Silks and half off Bloody Mary’s. To qualify, the guest must go to Player Services and receive a wristband after showing identification.
  • Free Play Drawing:
    • From 8 a.m.-6:50 p.m. guests aged 50+ must swipe their Oaklawn Rewards card at any promotional kiosk to activate their entries. 
    • Every guest who is 50+ is eligible for one entry.
    • Guests can earn also an additional entry for every 20 points earned on their Oaklawn Rewards card on the day of the promotion.
    • To be eligible for the final drawing, guests must swipe to activate their entries by 6:50 p.m.


  • The Fun Squad, beginning at 3 p.m., will draw three guests every 15 minutes. 
  • Each guest called will win $100 Free Play. 
  • If a Gold or Silver guest fails to show up, then the money will be added to the final drawing at 7 p.m.
  • Elite guests do not need to be present until the 7 p.m. drawing.
  • At 7 p.m., the Fun Squad will draw one player to win $100 Free Play plus any unclaimed prizes from that day.
  • At 7 p.m., the winner (Silver, Gold & Elite) MUST be present to collect their Free Play. 
  • Guests may only be drawn once between 3-6:45 p.m.
  • All guests are eligible for the final drawing at 7 p.m.


  • Winners will be picked randomly through a computer database system that counts all entries by all activated guests.
  • If the computer system goes down before/during a drawing, the drawing event will be delayed until the system comes back up.
  • At that time, the drawings will resume in the same time format as said event (example, if drawings are supposed to be every 15 min, then they’ll be every 15 min starting as soon as the system comes back up).
  • If drawings aren’t able to be completed on drawing day due to a system outage, Oaklawn will reschedule the drawings and will communicate the new date through signage.


From 8 a.m. to 10 p.m., guests aged 50+ qualify to earn 5x the entries for the $3,000 Travel Voucher Drawing on April 29. Entries will be earned for the end of the month drawing where 1 guest will win a $3,000 travel voucher. All casino guests will be eligible for this drawing but only Monday Funday participants will get 5x entries on Mondays.


For an official set of rules, please see Player Services.