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Winnipeg Predictions & Picks — July 23, 2026

By The Maiden Desk · July 23, 2026

Every pick below gets graded after the match — wins and misses both stay up.

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4 matches are on Thursday's card at Winnipeg, and we have a pick for every one of them. The headline act: August Holmgren against Liam Draxl in the round of 16. Our calls: Holmgren over Draxl, Chidekh over Matsuoka, Monday over Shimizu, Chan over Mochizuki. As always, every pick below is graded after the fact and stays up, right or wrong.

The boldest call on the card: Chan over Mochizuki — the market disagrees with us there.

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D. Chan vs. Shintaro Mochizuki

Thursday's Winnipeg round of 16 pits D. Chan against Shintaro Mochizuki on hard. D. Chan is 1-9 across recent matches. Shintaro Mochizuki has won 6 of the last 10.

The two have never played — a first meeting always adds a layer of uncertainty the numbers can't fully capture.

Neither the serve numbers nor the ratings separate these two by much, which is why our number stays close to even. A tiebreak or two would surprise nobody, with Chan fractionally more likely to land the big points.

Pick: ChanUpset call

Upset call — the market makes Mochizuki the favorite; our numbers say Chan.

Win probability: 56% Chan · Sets: 3 (43%) · most likely score 2-0 (33%)

✗ Pick wrongWe got this one wrong. Our final number was 56% on D. Chan; Shintaro Mochizuki won 6-2 2-6 6-4.

Johannus Monday vs. Yuta Shimizu

Thursday's Winnipeg round of 16 pits Johannus Monday against Yuta Shimizu on hard. Johannus Monday has won 6 of the last 10. Yuta Shimizu is 5-5 across recent matches.

This is the first career meeting between the two, which means no head-to-head baggage on either side of the net.

Hold strength tells the story — 74.5% versus 67.5% on first-serve points in Monday's favor. Monday should have enough here, though Shimizu has the tools to make the scoreboard uncomfortable.

Pick: Monday

Win probability: 67% Monday · Sets: 3 (44%) · most likely score 2-0 (38%)

✓ Pick rightNailed it. We had Johannus Monday at 67% before the match, and Johannus Monday won 4-6 6-3 6-3.

Clement Chidekh vs. Hayato Matsuoka

A spot in the next round is at stake on Thursday, when Clement Chidekh goes up against Hayato Matsuoka in the Winnipeg round of 16. Clement Chidekh comes in at 6 wins from the last ten. Hayato Matsuoka is 3-7 across recent matches.

The two have never played — a first meeting always adds a layer of uncertainty the numbers can't fully capture.

The serve is where this match separates: Chidekh has been winning 70.1% of first-serve points to Matsuoka's 67.1%, and on hard that gap compounds fast. The edge belongs to Chidekh — real, but not the kind you take for granted at this level.

Pick: Chidekh

Win probability: 61% Chidekh · Sets: 2 (61%) · most likely score 2-0 (38%)

✓ Pick rightWe got this one right. Clement Chidekh was our 61% pick, and won 6-3 7-6(4).

August Holmgren vs. Liam Draxl

August Holmgren and Liam Draxl meet in the round of 16 at Winnipeg on Thursday. August Holmgren is 6-4 across recent matches. Liam Draxl has won 6 of the last 10.

August Holmgren has had the better of this rivalry, winning 1 of 1 against Liam Draxl. On hard specifically it reads 1-0 Holmgren — worth more than the overall number this week.

Hold strength tells the story — 75.6% versus 70.4% on first-serve points in Holmgren's favor. Little separates them; Holmgren gets the nod on the finest of margins.

Pick: Holmgren

Win probability: 54% Holmgren · Sets: 3 (47%) · most likely score 2-0 (29%)

✗ Pick wrongMissed it — and it stays on the record. We had August Holmgren at 54%, but Liam Draxl won 7-5 1-6 6-4.

Updated Jul 23, 2026, 5:30 AM UTC. Picks are frozen before first serve and graded on the track record page — this page is never edited after the fact.