Four of them – Beakstown, Tokay Dokey, Molly The Dolly and Premier Rose – were trained by his brother, Dan, while Caroline Bailey provided the other with Crosspark.
Skelton’s nap-hand took his tally to 109 as he tries to keep tabs on the leader and current champion, Richard Johnson, in the jockeys’ title race.
“It’s brilliant. It’s my first five-timer and obviously it takes a lot of doing, so it’s something special,” the jockey said.
“It’s down to a lot of hard work and team work. Sometimes you have your ups, and sometimes your downs.
“We had the pain of losing a nice horse, Shantou Rock, two Saturdays ago and then you can have five winners the next weekend. Hopefully there were some nice horses there.
“The staff at home work hard and I’m very thankful to all of them.”
The trainer’s latest haul means he is closing in on £1million in total prize money, with £978,000 for the season and 114 winners.
Beakstown (5-4 favourite) got the ball rolling when he outpointed Southern Sam by two lengths in the two-and-a-half-mile maiden hurdle, before Crosspark (11-4 favourite) did the business by 16 lengths in the three-and-a-quarter-mile handicap chase.
After Tokay Dokey (4-7 favourite) had landed the odds in cosy fashion in the two-mile novice hurdle, it was the turn of Molly The Dolly (5-2 favourite) to keep the sequence going in the three-mile mares’ novice chase.
Premier Rose (5-1) capped a great day for the Skeltons when leading on the run-in to win the two-and-a-half-mile handicap hurdle.