Madden first won with Amadora in the $35,000 RBC Capital Markets Cup 1.50 metre competition. Madden was victorious again with Wrigly in the 1.45 metre jump off.
The 1.50-metre event was the feature event and was held in the winning round format.
Madden and Amadora, a 10-year-old Dutch Warmblood mare by Chin Chin x Indoctro owned by Abigail Wexner, were clear in the jump-off and able to set the winning time at 42.18 seconds, despite adding a stride to the last jump.
"For sure to the last fence I got a little Edward Scissorhands-ish there," said Madden. "I thought I was going pretty good until after the double combination. I could have been a little faster to the coin (jump) and for sure a lot faster to the last."
Second place went to Mexico's Enrique Gonzalez on Quilebo D Tillard, who were also clear in 43.79 seconds. American Meagan Nusz and Dynamo, owned by Amalaya Investments, were third in a time of 49.47 seconds.
Madden is second in the all-time money won list at Spruce Meadows, and her two wins Friday helped inch her toward first place, currently held by Canadian Olympic gold medallist Eric Lamaze.
Madden won this class last year with another mount, Mademoiselle.
Fifteen-year-old Lucas Porter rode Phineas to victory in the $10,000 Mercer Junior/Amateur 1.40 metre.