Kentucky Derby Saturday is one of the best betting days in horse racing every year, and this year is no exception. Florida Derby winner Fierceness is the 5-2 morning-line favorite in the 2024 Kentucky Derby odds, but he is a -145 favorite against Sierra Leone (+115) in a head-to-head matchup provided by Circa Sportsbook. That's just one of 50 head-to-head matchups available for the Derby. Post time is 6:57 p.m. ET.

With the Kentucky Derby annually presenting the toughest handicapping challenge of the year, you'll want to see what SportsLine writer Gene Menez has to say before making any Kentucky Derby head-to-head matchups considering his success with last year's head-to-head Kentucky Derby picks. Join SportsLine here to get his full Kentucky Derby picks and start winning!

A former reporter and editor at Sports Illustrated, Menez covered an array of sports, including horse racing, for the magazine and its website for almost 14 years. Between 2010 and 2012, he served as SI's handicapper for the Triple Crown races and correctly predicted Super Saver to win the Kentucky Derby in 2010.

In 2015, while writing for Sports on Earth, Menez accurately gave out the Kentucky Derby superfecta (American Pharoah, Firing Line, Dortmund and Frosted), which paid $1,268.20 for $2. Then in 2017, he tweeted out his Kentucky Derby picks, including Always Dreaming to win, and hit the Pick 4, which paid almost $6,900 on a $1 bet. Join SportsLine right here to see his shocking 2024 Kentucky Derby picks!

In a span of seven races last year for SportsLine, he cashed the winner of the Lecomte Stakes, the exacta in the Southwest Stakes ($468), the winner of the Holy Bull Stakes, the winner of the Sam F. Davis Stakes, and the trifecta in the Jenny Wiley Stakes. In May, he nailed National Treasure's win in the Preakness.

In addition, he went 4-1 with his five head-to-head Derby picks last year, earning +2.63 units.

Now, Menez has looked at the 2024 Kentucky Derby head-to-head matchups, made his picks and formulated his bets. Join SportsLine here to see them!

We can tell you that Menez is taking Mystik Dan (+105) to beat Resilience. "[Mystik Dan] has run multiple fast races, and he should get a terrific, ground-saving trip from the No. 3 post," Menez told SportsLine.

Menez has five other head-to-head picks, including an even bigger plus-money best bet at a "ridiculous price." You ABSOLUTELY NEED to see which horses they are before making any 2024 Kentucky Derby picks of your own!

So what head-to-head picks does Menez like for the 2024 Kentucky Derby? And what plus-money underdog is a must-back? ... Join SportsLine now to get the top 2024 Kentucky Derby picks and bets, all from the expert who went 4-1 with his five head-to-head Derby picks last year!