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Jenson Brooksby vs Stefanos Tsitsipas Betting Picks & Live Stream – Brooksby Has the Momentum to Trouble Tsitsipas in Winston-Salem
- Both players struggled for wins in 2026 and lack venue experience
- Brooksby has match sharpness after his first-round win
- Recommendation: Back Brooksby to win first set & cover +1.5 games
Jenson Brooksby plays a backhand against Adam Walton in Montreal
(credit: Getty)
Stefanos Tsitsipas and Jenson Brooksby have both struggled for wins for much of the 2026 season, while neither player has much experience at this venue, making it difficult to fully trust either of them. However, Brooksby played a first-round match on Sunday, giving him the advantage of better match sharpness and more familiarity with the conditions.
Brooksby Looks To End His Run Of Early Exits
- Brooksby has registered multiple main-draw wins only three times in 20 events this year.
- He has a 4–13 record against Top 50 players in 2026.
- Tsitsipas has a 17–3 record against players outside the Top 50 this year.
- He is looking to make his mark in Winston-Salem.
HTH - Jenson Brooksby leads 1-0
| Year | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2022 | Indian Wells | 3R | Hard | Jenson Brooksby | 1-6, 6-3, 6-2 |
Brooksby Looks to Extend His Winning Run
Jenson Brooksby kicked off his campaign with a straight-sets victory over Giovanni Mpetshi Perricard, 6-3, 6-2. He did not face a break point and converted four of the five break points he created during the match.
The American struggled significantly on tour earlier this year, failing to win a match in 11 of his first 14 events. However, his performances have been more encouraging in recent weeks.
He has cleared the opening-round hurdle in six of his last seven events, including this week, reaching the third round at Wimbledon, the quarterfinals in Acapulco and the second round in Montreal. He will now be looking to produce a deep run this week.
| Category | Details |
|---|---|
| Country | USA |
| Age | Born 26 October 2000 |
| Plays | Right-handed |
| World Ranking | No. 74 |
| Career High | No. 33 (13 June 2022) |
| Elo Ranking | No. 90 |
| Tour-Level Titles | 1 |
Tsitsipas Aims to Rediscover His Winning Form
Stefanos Tsitsipas dropped outside the Top 80 in the rankings a couple of months ago after struggling for consistency and form, but his title-winning run in Gstaad helped him return to the Top 50.
However, he has failed to build on that result in the following weeks. He has played three events during the North American swing so far and won only two main-draw matches, highlighting his continued struggles.
He has played 19 events this year, with his notable results including the fourth round in Madrid, the quarterfinals in Doha and the third round in Miami.
This is his second appearance in Winston-Salem. He made his debut last year but lost in the opening round to Bu Yunchaokete, and he will be looking for a better result this week.
| Category | Details |
|---|---|
| Country | Greece |
| Age | Born 12 August 1998 |
| Plays | Right-handed |
| World Ranking | No. 49 |
| Career High | No. 3 (09 August 2021) |
| Elo Ranking | No. 28 |
| Tour-Level Titles | 14 |
Verdict
Brooksby's extra match time could give him an early edge, especially against a player like Tsitsipas who has also struggled for consistency this season. He looks like the stronger option to make a quicker start and keep the opening set competitive.
Backing Jenson Brooksby to win the first set and cover the +1.5 games handicap in the first set.
Jenson Brooksby
1st Set Winner
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Brooksby +1.5
Handicap Games 1st Set
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