August Holmgren and Darian King will square off in the 1st round of the Chicago Challenger for the 2nd time in their career. They are scheduled to compete on Tuesday at 2:00 pm on CENTER COURT. In this post, we analyze their head to head performance and prediction.
Prediction, odds and live streaming
The pick for Tennis Tonic is August Holmgren who should win in 2 sets.
August Holmgren -> 1.3
Darian King -> 3.28
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Prediction and head to head August Holmgren vs. Darian King
This will be the 2nd time that August Holmgren and Darian King play each other. The head to head is 1-0 for Holmgren (see full H2H stats), 1-0 on hard.
The last time that they competed against each other, Holmgren won 6-3 6-0 in the qualifications in the Tiburon Challenger back in 2022.
August Holmgren
18 - 17win/loss
171
144
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 23-25 | 14-12 | 3-8 | 1-3 | 5-2 | 0-0 |
| 2024 | 37-25 | 24-12 | 6-6 | 7-7 | 0-0 | 0-0 |
| 2023 | 46-26 | 33-14 | 9-6 | 4-6 | 0-0 | 0-0 |
| 2022 | 31-12 | 18-4 | 10-5 | 3-3 | 0-0 | 0-0 |
| 2021 | 19-8 | 12-6 | 7-2 | 0-0 | 0-0 | 0-0 |
Ranked no. 144 (career-high), the Dane will start his run in the Chicago Challenger after he played his last match in the Lexington Challenger where he lost 6-7(5) 7-5 5-1 ret. to Mejia in the 1st round on the 28th of July.
August has an aggregate 17-17 win-loss record in 2025, 9-7 on hard (See FULL STATS).
His best result of the year was winning the title the Granby Challenger where he overcame Liam Draxl in the final 6-3 6-3.
Talking about his overall career, The Dane has an overall 196-111 record. He has a positive 122-57 record on hard.
Previously in the Chicago Challenger
August has never competed in this tournament before.
Darian King
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2025 | 8-8 | 6-8 | 2-0 | 0-0 | 0-0 | 0-0 |
| 2024 | 2-2 | 2-2 | 0-0 | 0-0 | 0-0 | 0-0 |
| 2023 | 33-10 | 17-7 | 10-0 | 6-3 | 0-0 | 0-0 |
| 2022 | 14-9 | 11-5 | 2-2 | 1-2 | 0-0 | 0-0 |
| 2021 | 11-14 | 6-7 | 4-4 | 1-2 | 0-1 | 0-0 |
Ranked no. 766, the Barbadian will start his run in the Chicago Challenger after he played his last match in M15 Santa Tecla where he lost 4-6 4-5 ret. to Lilov in the 1st round on the 16th of July.
The Barbadian has a compiled 5-3 win-loss record in 2025, 3-3 on hard (See FULL STATS).
In terms of his career, Darian has an overall 391-221 record. He has a positive 274-139 record on hard.
Tennis Scores in Chicago Challenger
- Naoki NakagawaNakagawa – Alfredo PerezPerez (6-4 6-3) – Stats, scores, rankings
- Garrett JohnsJohns – Billy HarrisHarris (3-6 6-3 6-4) – Stats, scores, rankings
- Yibing WuWu – Andre IlaganIlagan (1-6 6-2 6-1) – Stats, scores, rankings
- Beibit ZhukayevZhukayev – Patrick MaloneyMaloney (4-6 6-3 6-4) – Stats, scores, rankings
Upcoming matches in the draw
- Jason JungJung – (0-0) – H2H and prediction
- Alex BoltBolt – Tsung-Hao HuangHuang (0-0) – H2H and prediction
- Yibing WuWu – Naoki NakagawaNakagawa (0-0) – H2H and prediction
- August HolmgrenHolmgren – Darian KingKing (1-0) – H2H and prediction
- Andrew FentyFenty – Yu Hsiou HsuHsiou Hsu (0-0) – H2H and prediction
- Stefan DostanicDostanic – Bernard TomicTomic (0-1) – H2H and prediction