For the third time in two weeks, Daniil Medvedev will attempt to defeat Alexander Zverev. This time it’s in the ATP Finals championship match, and while Medvedev has won five straight against Zverev and appears to be poised to win a sixth, the psychology of defeating a player of Zverev’s caliber three times in 15 days should bring caution to potential bettors.

Defeating a quality opponent multiple times in a row is extremely difficult in any sport, but far more difficult in a one-on-one sport like tennis. Not only does Zverev have the two recent losses to learn from, but he will be able to swing more freely than ever knowing he nothing to lose—along with the confidence of beating world No. 1 Novak Djokovic, 7-6, 4-6, 6-3, in the semifinals on Saturday.

All that said, I’m not sure how you beat an in-form and motivated Medvedev on a quick indoor hard court. The world No. 2 has battled extreme adversity all tournament long, yet boasts a perfect 4-0 record.

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Medvedev clearly has Zverev's number, but defeating a quality opponent three times in a row is extremely difficult

Medvedev clearly has Zverev's number, but defeating a quality opponent three times in a row is extremely difficult

Hubert Hurkacz played to the best of his ability in his first-round match, winning an incredibly high quality first set 7-6, but Medvedev won the next two sets, 6-3, 6-4, and never faced a break point all match.

In his next round, Medvedev beat Zverev 6-3, 6-7, 7-6, all while dealing with an extremely questionable foot-fault call at 1-1 in the second-set tiebreak on his second serve. A past version of Medvedev may have focused too much on that call, yet he maintained his focus and aggression, ultimately prevailing.

After winning the first set 6-0 against Jannik Sinner in the first round, Medvedev survived a phenomenal performance in front of a boisterous Italian crowd, squeaking by 6-0, 6-7, 7-6. This victory was astounding, given Sinner’s incredible level, combined with the fact that Medvedev already advanced to the semifinals.

I have bet Medvedev all week long, and will continue to do so on Sunday, but I will lower the stakes by a significant amount, simply because beating a great player three times in 15 days is a massive mental challenge.

The Pick: Daniil Medvedev -2.5 games