Trey Hilderbrand and Joshua Sheehy will clash against each other in the qualifications of the Chicago Challenger for the 1^st time in their career. They are scheduled to compete on Monday at 11:00 am on COURT 1. Here the head to head stats and relative prediction.

Prediction, odds and live streaming

The pick for Tennis Tonic is Trey Hilderbrand who should win in 3 sets.

As per the initial odds, Trey Hilderbrand is the pick to win this match.
Trey Hilderbrand -> 1.58
Joshua Sheehy -> 2.26

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Prediction and head to head Trey Hilderbrand vs. Joshua Sheehy

There is no head to head record between Trey Hilderbrand and Joshua Sheehy since this will be the first time that they will face off in the main tour.

Trey Hilderbrand

Ranked no. 682, Hilderbrand got to the qualifications after beating Adhithya Ganesan 6-2 3-6 7-5.

In the qualifications, Hilderbrand defeated Ganesan (6-2 3-6 7-5). During the match, Hilderbrand scored 97 points vs Ganesan’s 87. Hilderbrand was quite aggressive to blast 42 winners.

Regarding the service games, Hilderbrand overpowered his opponent with 20 aces and he was not very solid on his 2nd serve to score 10 double faults. Trey Hilderbrand lost the serve twice and he saved 3 break points. Furthermore, Hilderbrand put 61% of his first serves in, winning 86% (42/49) of the points behind his 1st serve and 42% (13/31) on the 2nd serve. The American broke Ganesan 4 times after converting 36% of his break points (4/11).

Hilderbrand has a winning win-loss record in the last 7 years having won 59% of his matches (91-64). 4-5 on hard in 2025. Regarding his performance on the same surface of this competition, Hilderbrand has a compiled54-36 win-loss record in the last 7 years on hard.

Trey has a compiled 13-9 win-loss record in 2025, 4-5 on hard (See FULL STATS).

Previously in the Chicago Challenger

Trey has never competed in this tournament before.

Joshua Sheehy

Ranked no. 701, Joshua reached the qualifications after beating Alvin Nicholas Tudorica 7-5 6-2.

In the qualifications, Sheehy had a good straight sets win against Nicholas Tudorica (7-5 6-2). During the match Sheehy scored 82 points vs Nicholas Tudorica’s 62. Joshua was exceptionally aggressive to blast 23 winners.

About the serving games, Sheehy recorded 9 aces and he committed only 1 double fault for the entire match. Overall, Joshua Sheehy was quite effective on serve to win 74% (23/31) of his 1st serve and 59% (16/27) on the second serve. However, this didn’t prevent his to concede the serve twice. The American broke Nicholas Tudorica 5 times after converting 36% of his break points (5/14).

The American has an overall 12-12 win-loss record in 2025, 7-7 on hard (See FULL STATS).

H2H Performance in the tournament

Matches, sets, games and points

Points	Hilderbrand	Sheehy
Match played	1	1
Tot Set	3	2
Tot Games	29	20
Pts	97-87	82-62
Total Points	184	144
Winners	42	23
%Winners	43%	28%

Both Hilderbrand and Sheehy played 1 match. Also both players started their run from the qualifications.At the moment, Trey Hilderbrand conceded 1 set while Joshua Sheehy hasn’t dropped a set so far. Hilderbrand has played 1 set more than Sheehy (3 vs 2). Therefore, Hilderbrand played 9 games more than Sheehy. The American scored 42 winners (43% of the total points). On the other side, Joshua scored 23 winners (28%).

Serve Performance

Serve	Hilderbrand	Sheehy
Aces	20	9
Avg per match	20	9
1st in	49/80	31/58
%1st in	61%	53%
1st pts	42/49	23/31
%1st pts	86%	74%
2nd pts	13/31	16/27
%2nd pts	42%	59%

Hilderbrand bagged 20 aces . Sheehy struck 9 aces . Hilderbrand won 86% points behind his first serve. He extremely effective on his second serve to win 42% of the points. On the other side, Sheehy won 74% of the points behind his first serve. He had a solid display on his second serve to win 59% of the points.

How they played the important points

Breaks	Hilderbrand	Sheehy
Won	4	5
Converted	4/11	5/14
% Converted	36%	36%
Conceded	5	3
Saved	3	1
% Saved	60%	33%
Times Broken	2	2

The American broke his opponent 4 times with a 36% conversion rate. Trey conceded his serve twice and he saved 60% of the break points that he conceded. Sheehy broke his opponent 5 times with a 36% conversion rate. Joshua conceded his serve twice and he saved 33% of the break points that he conceded.

Hilderbrand
	Q1 Ganesan	Total
Score	6-2 3-6 7-5
Tot Set	3	3
Tot Games	29	29
pts	97-87	97-87
Total points	184	184
Winners	42	42
%Winners	43%	43%
SERVE
Aces	20	20
Double Faults	10	10
1st in	49/80	49/80
% 1st in	61%	61%
1st pts	42/49	42/49
% 1st pts	86%	86%
2nd pts	13/31	13/31
% 2nd pts	42%	42%
Breaks
Won	4	4
Converted	4/11	4/11
Converted %	36%	36%
Conceded	5	5
Saved	3/5	3
Saved %	60%	60%
Times Broken	2	2

Sheehy
	Q1 Nicholas	Total
Score	7-5 6-2
Tot Set	2	2
Tot Games	20	20
pts	82-62	82-62
Total points	144	144
Winners	23	23
%Winners	28%	28%
SERVE
Aces	9	9
Double Faults	1	1
1st in	31/58	31/58
% 1st in	53%	53%
1st pts	23/31	23/31
% 1st pts	74%	74%
2nd pts	16/27	16/27
% 2nd pts	59%	59%
Breaks
Won	5	5
Converted	5/14	5/14
Converted %	36%	36%
Conceded	3	3
Saved	1/3	1
Saved %	33%	33%
Times Broken	2	2

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