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Winnipeg Predictions & Picks — July 23, 2026

By The Maiden Desk · July 23, 2026

Every number below was fixed before the match and graded against the official result.

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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.

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

D. Chan vs. Shintaro Mochizuki

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

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%)

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.

Johannus Monday vs. Yuta Shimizu

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

Pick: Monday

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

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.

Clement Chidekh vs. Hayato Matsuoka

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

Pick: Chidekh

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

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.

August Holmgren vs. Liam Draxl

✗ Pick wrongMissed it. We had August Holmgren at 54%, but Liam Draxl won 7-5 1-6 6-4.

Pick: Holmgren

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

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.

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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.