Daniel Milavsky and Anton Shepp will fight against each other in the qualifications of the Winnipeg Challenger for the 1st time in their career. They are scheduled to compete on Monday at 11:00 am on COURT 1. 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 Daniel Milavsky who should win in 3 sets.
As per the initial odds, Daniel Milavsky is the pick to win this match.
Daniel Milavsky -> 1.833
Anton Shepp -> 1.85
Here where top tennis events are broadcasted or streamed online (ATP, WTA).
At the challenger level, there will be free live streaming on Challenger TV.
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Prediction and head to head Daniel Milavsky vs. Anton Shepp
There is no head to head record between Daniel Milavsky and Anton Shepp since this will be the first time that they will clash against each other in the main tour.
Daniel Milavsky
31 - 17win/loss
312
306
LLLWWWLWWW | Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2026 | 38-22 | 18-14 | 1-2 | 15-5 | 4-1 | 0-0 |
| 2025 | 44-22 | 30-15 | 1-1 | 13-5 | 0-1 | 0-0 |
| 2024 | 12-3 | 3-2 | 2-1 | 7-0 | 0-0 | 0-0 |
| 2023 | 8-4 | 7-4 | 1-0 | 0-0 | 0-0 | 0-0 |
| 2022 | 1-2 | 1-1 | 0-1 | 0-0 | 0-0 | 0-0 |
Ranked no. 326 (career-high), Daniel got to the qualifications after defeating Thomas Fancutt 6-4 3-6 7-5.
In the qualifications, Daniel defeated Fancutt (6-4 3-6 7-5). During the match, Milavsky scored 89 points vs Fancutt’s 79. Daniel was quite aggressive to blast 42 winners.
Regarding the service games, Milavsky bagged 5 aces and he committed only 5 double faults. Overall, Daniel Milavsky was quite efficient on serve to win 86% (42/49) of his 1st serve and 63% (15/24) on the second serve. However, this didn’t prevent his to concede the serve once. The American broke Fancutt twice after converting 40% of his break points (2/5).
Milavsky has a solid match record in the last 5 years having won 66% of his matches (95-48). 10-9 on hard in 2026. Talking about his performance on the same surface of this tournament, Milavsky has a composed51-31 record in the last 5 years on hard.
The American’s best result of the year was reaching the final in M15 Villahermosa.
The American has a composed 30-17 win-loss record in 2026, 10-9 on hard (See FULL STATS).
Previously in the Winnipeg Challenger
Milavsky has never competed in this tournament before.
Anton Shepp
| Year | Total | Hard | Clay | I.hard | Grass | Carpet |
|---|---|---|---|---|---|---|
| 2026 | 37-19 | 30-14 | 2-1 | 5-4 | 0-0 | 0-0 |
| 2025 | 35-14 | 27-10 | 8-4 | 0-0 | 0-0 | 0-0 |
| 2024 | 6-6 | 6-6 | 0-0 | 0-0 | 0-0 | 0-0 |
| 2023 | 9-4 | 9-4 | 0-0 | 0-0 | 0-0 | 0-0 |
| 2022 | 1-2 | 1-2 | 0-0 | 0-0 | 0-0 | 0-0 |
Ranked no. 494 (career-high), the Kiwi reached the qualifications after defeating Alexander Rozin 6-4 3-6 6-2.
In the qualifications, The Kiwi defeated Rozin (6-4 3-6 6-2). During the match Shepp scored 78 points vs Rozin’s 72. Shepp was exceptionally aggressive to blast 36 winners.
About the serving games, Shepp made 9 aces and he committed only 3 double faults. Overall, Anton Shepp was very efficient on serve to win 73% (36/49) of his 1st serve and 66% (19/29) on the second serve. However, this didn’t prevent his to concede the serve once. The Kiwi broke Rozin 3 times after converting 60% of his break points (3/5).
Shepp’s best result of the year was reaching the final in M15 Monastir and M15 Nakhon Pathom.
Shepp has a compiled 36-11 win-loss record in 2026, 29-8 on hard (See FULL STATS).
H2H Performance in the tournament
Matches, sets, games and points
| Points | Milavsky | Shepp |
|---|---|---|
| Match played | 1 | 1 |
| Tot Set | 3 | 3 |
| Tot Games | 31 | 27 |
| Pts | 89-79 | 78-72 |
| Total Points | 168 | 150 |
| Winners | 42 | 36 |
| %Winners | 47% | 46% |
Both Milavsky and Shepp played 1 match. Also both players started their run from the qualifications.Both players lost a set in the event. Daniel Milavsky dropped 1 set, while Anton Shepp dropped 1 set. Talking about their workload, Milavsky and Shepp have played the same amount of sets 3. However, Milavsky played 4 games more than Shepp. Daniel scored 42 winners (47% of the total points). On the other side, Anton fired 36 winners (46%).
Serve Performance
| Serve | Milavsky | Shepp |
|---|---|---|
| Aces | 5 | 9 |
| Avg per match | 5 | 9 |
| 1st in | 49/73 | 49/78 |
| %1st in | 67% | 63% |
| 1st pts | 42/49 | 36/49 |
| %1st pts | 86% | 73% |
| 2nd pts | 15/24 | 19/29 |
| %2nd pts | 63% | 66% |
Milavsky made 5 aces . Shepp made 9 aces . Milavsky won 86% points on his first serve. He very solid his second serve to win 63% of the points. On the other side, Shepp won 73% of the points on his first serve. He had a solid display on his second serve to win 66% of the points.
How they played the important points
| Breaks | Milavsky | Shepp |
|---|---|---|
| Won | 2 | 3 |
| Converted | 2/5 | 3/5 |
| % Converted | 40% | 60% |
| Conceded | 1 | 8 |
| Saved | 0 | 7 |
| % Saved | 0% | 88% |
| Times Broken | 1 | 1 |
Daniel broke his opponent twice with a 40% conversion rate. Daniel lost his serve once and he saved 0% of the break points that he conceded. Anton broke his opponent 3 times with a 60% conversion rate. The Kiwi conceded his serve once and he saved 88% of the break points that he conceded.
| Milavsky | |||
| Q1 Fancutt |
Total | ||
|---|---|---|---|
| Score | 6-4 3-6 7-5 | ||
| Tot Set | 3 | 3 | |
| Tot Games | 31 | 31 | |
| pts | 89-79 | 89-79 | |
| Total points | 168 | 168 | |
| Winners | 42 | 42 | |
| %Winners | 47% | 47% | |
| SERVE | |||
| Aces | 5 | 5 | |
| Double Faults | 5 | 5 | |
| 1st in | 49/73 | 49/73 | |
| % 1st in | 67% | 67% | |
| 1st pts | 42/49 | 42/49 | |
| % 1st pts | 86% | 86% | |
| 2nd pts | 15/24 | 15/24 | |
| % 2nd pts | 63% | 63% | |
| Breaks | |||
| Won | 2 | 2 | |
| Converted | 2/5 | 2/5 | |
| Converted % | 40% | 40% | |
| Conceded | 1 | 1 | |
| Saved | 0/1 | 0 | |
| Saved % | 0% | 0% | |
| Times Broken | 1 | 1 | |
| Shepp | |||
| Q1 Rozin |
Total | ||
|---|---|---|---|
| Score | 6-4 3-6 6-2 | ||
| Tot Set | 3 | 3 | |
| Tot Games | 27 | 27 | |
| pts | 78-72 | 78-72 | |
| Total points | 150 | 150 | |
| Winners | 36 | 36 | |
| %Winners | 46% | 46% | |
| SERVE | |||
| Aces | 9 | 9 | |
| Double Faults | 3 | 3 | |
| 1st in | 49/78 | 49/78 | |
| % 1st in | 63% | 63% | |
| 1st pts | 36/49 | 36/49 | |
| % 1st pts | 73% | 73% | |
| 2nd pts | 19/29 | 19/29 | |
| % 2nd pts | 66% | 66% | |
| Breaks | |||
| Won | 3 | 3 | |
| Converted | 3/5 | 3/5 | |
| Converted % | 60% | 60% | |
| Conceded | 8 | 8 | |
| Saved | 7/8 | 7 | |
| Saved % | 88% | 88% | |
| Times Broken | 1 | 1 | |
Head 2 Head
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