Yibing Wu and Naoki Nakagawa will play each other in the 2^nd round of the Chicago Challenger for the 1^st time in their career. They are scheduled to compete on Wednesday at 3:00 pm on CENTER COURT. In the following lines you can find the head to head analysis and prediction.

Prediction, odds and live streaming

The pick for Tennis Tonic is Yibing Wu who should win in 2 sets.

As per the initial odds, Yibing Wu is the pick to win this match.
Yibing Wu -> 1.098
Naoki Nakagawa -> 6.1

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Prediction and head to head Yibing Wu vs. Naoki Nakagawa

There is no head to head record between Yibing Wu and Naoki Nakagawa since this will be the first time that they will play each other in the main tour.

Yibing Wu

Ranked no. 186, Yibing got to the 2^nd round after beating Andre Ilagan 1-6 6-2 6-1.

In the 1^st round against Ilagan, Wu recovered from a 1-set down deficit before winning (1-6 6-2 6-1). During the match, Wu scored 62 points vs Ilagan’s 52. Yibing was quite aggressive to blast 28 winners.

Regarding the service games, Wu fired 3 aces and he committed only 3 double faults. Overall, Yibing Wu was pretty efficient on serve to win 74% (28/38) of his 1st serve and 55% (11/20) on the second serve. However, this didn’t prevent his to concede the serve 3 times. Yibing broke Ilagan 5 times after converting 63% of his break points (5/8).

Wu has a solid win-loss record in the last 8 years having won 64% of his matches (139-77). 17-4 on hard in 2025. Talking about his performance on the same surface of this event, Wu has an aggregate86-51 match record in the last 8 years on hard.

His best result of the current year was conquering the title the Tyler Challenger where he overcame Yi Zhou in the final 6-4 3-6 6-3.

The Chinese has a compiled 19-6 win-loss record in 2025, 17-4 on hard (See FULL STATS).

Previously in the Chicago Challenger

The Chinese has never competed in this tournament before.

Naoki Nakagawa

Ranked no. 350, Naoki got to the 2^nd round after beating Alfredo Perez 6-4 6-3.

In the 1^st round, The Japanese had a good straight sets win against Perez (6-4 6-3). During the match Nakagawa scored 74 points vs Perez’s 66. Naoki was very aggressive to blast 32 winners.

About the serving games, Nakagawa recorded 2 aces and he committed only 3 double faults. Naoki Nakagawa was quite efficient on serve to win 76% (32/42) of his 1st serve and 52% (17/33) on the second serve. This was the main reason for not conceding a single break during the match. Naoki broke Perez twice after converting 22% of his break points (2/9).

Nakagawa’s best result of the year was getting to the semifinal in M25 Timaru.

Naoki has a composed 9-15 win-loss record in 2025, 9-14 on hard (See FULL STATS).

Previously in the Chicago Challenger

Previously, his best result was reaching the qualifications in 2024. See his history

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H2H Performance in the tournament

Matches, sets, games and points

Points	Wu	Nakagawa
Match played	1	1
Tot Set	3	2
Tot Games	22	19
Pts	62-52	74-66
Total Points	114	140
Winners	28	32
%Winners	45%	43%

Both Wu and Nakagawa played 1 match. At the moment, Yibing Wu surrendered 1 set while Naoki Nakagawa hasn’t conceded a set so far. Wu has played 1 set more than Nakagawa (3 vs 2). Therefore, Wu played 3 games more than Nakagawa. Wu scored 28 winners (45% of the total points). On the other side, The Japanese fired 32 winners (43%).

Serve Performance

Serve	Wu	Nakagawa
Aces	3	2
Avg per match	3	2
1st in	38/58	42/75
%1st in	66%	56%
1st pts	28/38	32/42
%1st pts	74%	76%
2nd pts	11/20	17/33
%2nd pts	55%	52%

Wu scored 3 aces . Nakagawa scored 2 aces . Wu won 74% points behind his first serve. He extremely effective on his second serve to win 55% of the points. On the other side, Nakagawa won 76% of the points on his first serve. He had a solid display on his second serve to win 52% of the points.

How they played the important points

Breaks	Wu	Nakagawa
Won	5	2
Converted	5/8	2/9
% Converted	63%	22%
Conceded	4	5
Saved	1	5
% Saved	25%	100%
Times Broken	3	0

Wu broke his opponent 5 times with a 63% conversion rate. Yibing surrendered his serve 3 times and he saved 25% of the break points that he conceded. Naoki broke his opponent twice with a 22% conversion rate. Nakagawa was rock solid on his serve as he has never conceded a single service game after saving 5 break points.

Wu
	R1 Ilagan	Total
Score	1-6 6-2 6-1
Tot Set	3	3
Tot Games	22	22
pts	62-52	62-52
Total points	114	114
Winners	28	28
%Winners	45%	45%
SERVE
Aces	3	3
Double Faults	3	3
1st in	38/58	38/58
% 1st in	66%	66%
1st pts	28/38	28/38
% 1st pts	74%	74%
2nd pts	11/20	11/20
% 2nd pts	55%	55%
Breaks
Won	5	5
Converted	5/8	5/8
Converted %	63%	63%
Conceded	4	4
Saved	1/4	1
Saved %	25%	25%
Times Broken	3	3

Nakagawa
	R1 Perez	Total
Score	6-4 6-3
Tot Set	2	2
Tot Games	19	19
pts	74-66	74-66
Total points	140	140
Winners	32	32
%Winners	43%	43%
SERVE
Aces	2	2
Double Faults	3	3
1st in	42/75	42/75
% 1st in	56%	56%
1st pts	32/42	32/42
% 1st pts	76%	76%
2nd pts	17/33	17/33
% 2nd pts	52%	52%
Breaks
Won	2	2
Converted	2/9	2/9
Converted %	22%	22%
Conceded	5	5
Saved	5/5	5
Saved %	100%	100%
Times Broken	0	0

Tennis Scores in Chicago Challenger

• Hady HabibHabib – Kyle KangKang (7-6⁷ 6-3) – See score progression
• Karue SellSell – Miguel TobonTobon (6-4 6-3) – See score progression
• Michael ZhengZheng – Rodrigo Pacheco MendezPacheco Mendez (7-6⁷ 6-2) – See score progression
• Yu Hsiou HsuHsiou Hsu – Andrew FentyFenty (6-2 6-2) – See score progression
• August HolmgrenHolmgren – Darian KingKing (6-4 6-4) – See score progression
• Giles HusseyHussey – Martin DammDamm (7-6² 7-5) – See score progression
• Alex BoltBolt – Tsung-Hao HuangHuang (6-1 7-6⁷) – See score progression
• Stefan DostanicDostanic – Bernard TomicTomic (6-7³ 7-6⁴ 2-0 ret.) – See score progression
• Yi ZhouZhou – Joshua SheehySheehy (6-3 6-2) – See score progression
• Trevor SvajdaSvajda – Jason JungJung (6-3 7-6⁷) – See score progression
• Antoine GhibaudoGhibaudo – Adolfo Daniel VallejoDaniel Vallejo (6-0 6-2) – See score progression
• Samir BanerjeeBanerjee – Alex RybakovRybakov (6-2 6-3) – See score progression
• Naoki NakagawaNakagawa – Alfredo PerezPerez (6-4 6-3) – See score progression
• Beibit ZhukayevZhukayev – Patrick MaloneyMaloney (4-6 6-3 6-4) – See score progression
• Yibing WuWu – Andre IlaganIlagan (1-6 6-2 6-1) – See score progression
• Garrett JohnsJohns – Billy HarrisHarris (3-6 6-3 6-4) – See score progression

Upcoming matches in the draw

• Karue SellSell – Yu Hsiou HsuHsiou Hsu (0-0) – H2H and prediction
• Alex BoltBolt – Garrett JohnsJohns (1-0) – H2H and prediction
• Yibing WuWu – Naoki NakagawaNakagawa (0-0) – H2H and prediction
• August HolmgrenHolmgren – (0-0) – H2H and prediction
• Beibit ZhukayevZhukayev – (0-0) – H2H and prediction