Both boys tennis standouts had worked their way through their collective brackets to claim the No. 1 singles championships. Both had come up short the year before, Schilling falling in the Class 5A final while Wilcox got tripped up in 4A semis.
After winning their championships in 2019, they have a chance to accomplish something that hasn't been done in over 20 years.
The last time that both the 5A and 4A boys No. 1 singles champions won back-to-back championships the same year was during the 1998 and 1999 seasons. Cherry Creek's Chad Harris and Kent Denver's Cory Ross won their titles together in those two years. Schilling and Wilcox weren't even born.
Since then, the 5A No. 1 singles position has seen a repeat champion four times in Fruita Monument's Richard Johnson (2002-03), Rocky Mountain's Casey MacMaster (2008-09), Highlands Ranch's Hayden Sabatka (2011-12) and Chatfield's Christian Holmes (2017-18). In 4A there has only been one back-to-back champion since Ross and that was his little brother Casey in 2015-16. Niwot did get a two-champion in Harrison Lang but he won his titles in 2010 and 2012 with a loss in the championship match to Kent's David Mitchell in 2011.
As the boys tennis season enters its full swing now, Wilcox and Schilling will attempt to tie their names together in a way that's over two decades in the making.
"That's amazing," Wilcox said. "It's motivational and I would love to be a part of any kind of small history that I can."
The catch is that both players know that nothing is a given simply because they won a title the year before. Both have suffered defeats late in the bracket and both have seen talented senior players fall in either the semifinals or the championship final.
The key, according to both players, is to maintain focus and act as though each opponent on the court is more than capable of ending their championship runs.
"My mentality is to take it one match at a time," Schilling said. "I'm not thinking about regionals or state. I have to get there first. Just because I found success last year and won state, it doesn't mean I'm guaranteed that."
The good news is their seasons are off to a good start. Both players have a few dual matches under their belt and neither has dropped a match yet. Wilcox is especially dominant as he's only dropped one game all season. His talent is demonstrating that he has what it takes to make another run at Pueblo City Park.
"My strength is my versatility," he said. "I feel like I can do anything on the court. No matter what position I'm put in, I always feel like I have a way out."
He proved that in his championship winning match after dropping the first set to Cheyenne Mountain's Joey Geisz. Wilcox rallied to win the match 2-6, 6-2, 6-2.
Schilling's lone dropped set of his season came in a Sept. 30 win over Cherry Creek's George Cavo. He rallied to win that one in three sets and never dropped a set for the remainder of the season. Like Wilcox, Schilling knows that the path to another championship - and the path at a chance at shared history with the Niwot senior - lies with how dominant he needs to be, not how dominant he has been.
"I've know George and (Fairview's) Luke (Silverman) for a long time," Schilling said. "These aren't new faces from last year or anything. George and I are really good friends and we know how each other play."
Regardless, when Wilcox and Schilling take the court, all friendships are put on pause. They've exhibited nothing but great sportsmanship in their time with their schools, but they both have the same mission in mind. Should they each come away with another championship, that accomplishment will tie them together in Colorado high school tennis history.