But now, their plan might have wider implications.
Webb and Drennon have been invited to participate in the U.S. Army All-American Bowl combine in early January in San Antonio.
In addition, Webb and Drennon already have a combined 15 scholarship offers from college programs, including several schools that have expressed interest in both players.
So they could end up in the same place in another way - at the same major college.
"That's a high possibility," Drennon said. "We'll probably take a lot of our visits together. I wouldn't be surprised if we both went to the same school."
For now, the players say they are focused on Friday night's showdown between Timber Creek and visiting Woodrow Wilson, a clash of 4-0 teams in a WJFL interdivision battle.
"That's going to be one of the best games of the year," Webb said.
But the invitation to the combine, where they will be joined by many of the country's top juniors and sophomores, caught both players by surprise.
"I never was expecting it," Drennon said. "It means a lot. It shows what people think of us as players and our potential. I want to spend the rest of the year proving that I deserve to go."
The 6-foot-4, 225-pound Drennon is a former basketball star who projects as a pass-rushing defensive end. The 6-2, 295-pound Webb, who also is a star wrestler, projects as an interior defensive lineman, perhaps a nose tackle.
Webb also could project as an interior offensive lineman. He also was invited to participate in the Under Armour national combine, which will held in Orlando in late December.
"I might just fly from Orlando to San Antonio," Webb said. "It's a great honor, especially to be going with 'Dre [Drennon]."
The combine in San Antonio will be held in conjunction with the U.S. Army All-American Bowl, a nationally televised senior all-star game that will be held Jan. 7 in the Alamodome.
The three-day combine event is modeled after the NFL combine, with speed and strength testing and competitive drills.
Webb has received 10 scholarship offers, said Timber Creek coach Rob Hinson. Drennon has received five.
All five of the schools that have extended offers to Drennon - Penn State, Iowa, Rutgers, Syracuse, and Purdue - also have made offers to Webb, leading to the possibility that the players could end up together.
"I think it's a real possibility," said Webb, who also has offers from Tennessee, Connecticut, Michigan State, North Carolina State, and Central Florida.
"We're building chemistry every day. I could see us ending up at the same school and lining up next to each other for the same defense."
Contact staff writer Phil Anastasia at 856-779-3223, panastasia@phillynews.com, or @PhilAnastasia on Twitter. Read his blog, "Jersey Side Sports," at www.philly.com/jerseysidesports