Isaac Toivonen will be Red Wing's first state entrant since 2007 when he steps on the court Thursday morning at the Baseline Tennis Center on the University of Minnesota campus in Minneapolis.
His road to the Class 2A boys state tennis tournament was mostly smooth, save for a 6-4, 7-6 (2) loss in the Section 1AA finale, but Toivonen knows his first-round opponent Thursday, Eagan's Zach Ekstein, will be his toughest test to date.
"He's a really consistent player," Toivonen said. "When he played (Red Wing's) George Gabrielson a few years ago, I don't think he missed. ... Definitely, he's going to be the best opponent I've faced all year."
Ekstein, ranked second for Class 2A in the Minnesota Tennis Coaches Association poll, rolled through Section 3AA with four straight set victories. He dropped eight games total in four matches, including a 6-3, 6-1 win in the section final against Burnsville's Thomas McCallie, the ninth-ranked player in Class 2A. Ekstein is seeded fourth in the state bracket.
"Isaac's going to have to bring his 'A' game or his 'A-plus' game to beat him," Red Wing head coach Matt Kavanagh said. "Isaac's got a bigger serve but the consistency might not be there. I think his second serve will be just as effective. The key will be to leave an impression. He doesn't want the point to go on too long. He needs to try to leave an impression with his serve and his second shot."
Toivonen said he received some pointers from Lakeville South's Chase Roseth, who played Ekstein earlier in the year and said he lost 6-1, 7-5.
"He was telling me some strategies to beat him or play better against him, at least," Toivonen said. "Any advantage I can get versus Ekstein would be good."
With his size advantage, Toivonen will hope to end some points quickly at the net but he also creates tough passing angles that force errors.
"Anytime you've got someone stretched and you're at the net, you're at a big advantage," Kavanagh said. "We need to set that up quickly. The serve and volley tactic might be something he can throw in once per game."
Ekstein's consistency and strength at the baseline means Toivonen can't just float the ball back into the middle of the court. Toivonen will need to take more chances and hit his spots to take away Ekstein's time to measure shots.
"He has to take his opportunities when they present themselves," Kavanagh said. "He's going to have to redline his game, he's going to have to take more risks than he's used to, but the problem is you're risking more; you're risking more unforced errors. Otherwise he'll be beaten slowly as opposed to going out on his own terms.
"It's a winnable match," Kavanagh added. "The difference between the good players and the great players is just time. How well they get to the ball and how much time they give themselves. If you take away time, you can make anyone look ordinary."
Taking down a seeded player is a tall order but Toivonen said he is confident that the possibility is there if he plays well. Thursday's match begins at 8 a.m. and Toivonen will play a second match at noon regardless of outcome.
"I'm going into the match not confident but knowing I have a chance," he said. "If you always go into a match thinking you're going to have a chance, you will."