While Smith's two success from four rounds of the competition, which featured 14 invited riders from around the globe, saw him out on his own in front, Lisa Allpress had already achieved a notable milestone in the opening leg, the $400,000 stc Dare, as she became the first female jockey to ride a winner in Saudi Arabia.
The multi-decorated 54-year-old, who boasts the 2018 Triple Crown among his numerous honours, stole an easy lead in round two, the $400,000 stc Cloud over 1600m, aboard the Saleh Suliman Alhamd-owned Sun Hat which he never looked likely to relinquish.
Then in round three, the $400,000 stc Pay over 1800m, he again finished well clear aboard the consistent Paris, in the colours of Sharaf Mohammed S. Al Hariri.
"At my age I'm stoked to win this jockeys challenge," said Smith. "I'm so happy and very blessed. I was hoping to do well in the challenge and then we have the Saudi Cup tomorrow and I'm really, really looking forward to tomorrow. I think my filly tomorrow in the Saudi Cup, Midnight Bisou is going to love this track, she acts like she will.
"I'm proud to start the time I'm here off by winning tonight in great fashion. I'll be back, I love this place and I love that dirt course out there. It's the best dirt course I've been on.
It's very kind and very good for a horse and America should really take a look at this surface. Man, it's kind and when it feels kind it is kind. I absolutely loved it."
Lisa Allpress was one of seven female jockeys making their debuts in Saudi Arabia and she was delighted to be part of the event.
A multiple champion in her homeland of New Zealand, Allpress had to wait until late in the day as Olivier Peslier, riding Motayammen, was in full control in the lead. However, with 400m remaining, his horse began to falter and Allpress, riding Matmon, began to close.
Just before the line, Matmon put his head past Motayammen and Allpress, wearing the white colours of King Abdullah Bin Abdulaziz Sons, punched her fist in celebration.
"I came here with no expectations, I just wanted to enjoy the experience, but we have been very well looked after and I want to thank everyone who has organised it," said Allpress.
"That means a lot. I'm just so thankful to get the invite to come here.
"Where I come from it's not a crazy thing for a woman to be riding in the big races but this means a lot. I'm just happy to be here and doing my thing. I came here with an open mind and I'm extremely thankful to be asked.
"I had a good chat with Mr. (Phil) Tuck and the handicapper (Phil Smith) and we went through my rides and it basically made me relax and go out there and have fun. It's very ground-breaking and I can't believe it, it's very special."
The concluding round saw Swiss-born, German-based Sibylle Vogt join the honours board as she edged a very tight finish to the $400,000 stc 5G over 1200m. A strong ride on Sabeq'hom saw her hold off Canadian Emma-Jayne Wilson and Alshatherwan.
Vogt also took second position in the overall results with 29 points, with Smith picking up 33.
She said: "It's really nice to win on a night like this. I was so excited to be here and the night was so special, and for three women to be in the top places (second and a tie for third) is great."
Mickaelle Michel tied for third with Allpress on 15 points.
The rest of the riders were delighted to have taken part.
Michel said: "It was a really great event with so many nice people. It's a nice big track and it was an honour to be invited. I'm really happy now."
Frankie Dettori said: "It's fun. I enjoy it - they're racing for $1.6 million!"
Sophie Doyle said: "The event is great. They're showcasing fabulous jockeys. It's great for the women to be here. For Lisa (Allpress) to have won the first race of the jockey challenge, you couldn't have asked for anything better. (She was) the first female to ride (a race) on the track and to have won it was great."
Irad Ortiz said: "I'm having fun, they're treating us really well, I'm enjoying it."
Wilson said: "Jockey challenges are unique, I've ridden in them all over the world, it's always a pleasure to be invited. For the first time with an event like this, to have it go like this, is fantastic.
"To have an event like this the day before your biggest day is not easy - hands down fantastic job. The competition itself - on a surface like this against this calibre of riders and at such a wonderful facility - just adds to the atmosphere. It's been an absolute pleasure and honour to participate and I'm really happy that I came."