That would take the two not only through Saturday's Central Coast Section Championships at Toro Park in Salinas but the CIF State Championships at Woodward Park in Fresno on Nov. 27.
There's a very good chance that either runner will run the Division V individual title on Saturday. After all, a runner from Castilleja or Priory has won for the past eight years. Don't be surprised if both teams also qualify, which generally is the case, as well.
Gregory, junior, is the defending CCS Division V champion. She won last season in 19.07 at Crystal Springs in Belmont while helping the Panthers win the team title. Skokowski was second in 19:35, helping the Gators finish third and also qualify for the state finals.
In 2008, the last time the section finals were held at Toro Park, it was Skokowski's time to shine. She won the individual crown in 20:21 to help Castilleja win the team title. Gregory, then a freshman, finished third in 21:01 while the Panthers grabbed second in the team race.
In Skokowski's freshman season in 2007, she finished sixth in 20:44 at Crystal but the Gators won the team title. Then-freshman Devon Errington of Priory won individual title to help her team take second.
Based on performances this season, it appears Gregory is ready to take back the title. She captured the West Bay Athletic League crown last Friday in 18:52 over the 2.95 Crystal Springs course while Skokowski was second in 19:08. It has been that way all season as the two have dominated in their league competitions.
"I had my lucky pink shoes," Gregory said as perhaps why she won the WBAL title.
Gregory came in as the heavy favorite, having won three times in league-wide meets prior to Friday.
"It's sort of an uncomfortable position for me," Gregory said of the favorite's role. "I'd rather be the underdog. But, today it was more about us doing well (as a team). I had to push myself. I don't think we were looking to win the team title, it was more just to move on."
Gregory actually missed two weeks of training to prevent a possible stress fracture, returning just this week.
"I had two days of practice and then the meet," she said. "My coaches had confidence in me that I'd be able to pull through. So, I'm happy to be here."
While the Priory and Castilleja girls battle it out, another showdown looms in the CCS Division I girls' race on Saturday between Carlmont and Gunn. The Titans are the defending champions, but Gunn coach Ernie Lee knows last year's effort means little.
"Carlmont is the favorite, especially after what they ran at their league finals compared to how we ran," Lee said. "We're just hoping to have everyone run their best race of the year. San Benito has been running very well lately, so they could also challenge for a state meet berth."
In Division I, only the top two boys' and girls' teams qualify for state. In Division V, it's three each. Division II has three each while Division IV advances two boys' teams and three girls'.
Jessie Petersen of Carlmont returns to defend her Division I title while Gunn senior Erin Robinson is back to improve upon her runnerup finish last season. The Titans put five runners among the first 13 in 2009, but two of those were seniors. Junior Kieran Gallagher is back after taking sixth and senior Emma Dohner returns after finishing 13th. The big addition to Gunn's team is freshman Sarah Robinson, Erin's sister who finished third while Erin took second at the SCVAL El Camino Division finals two weeks ago.
Carlmont and Gunn are the only Division I girls' teams among the top 10, and thus appear to have the best chance of advancing.
The Menlo-Atherton boys also have a shot of advancing to the state finals, but is running in a tough Division I field that includes No. 1-ranked Bellarmine, No. 4 Carlmont and No. 5 San Benito, The Bears are No. 6 overall and fourth in Division I while the Gunn boys are No. 10 overall and No. 6 in Division I.
The Palo Alto girls have an outside shot in Division I, where they are the No. 4-ranked squad.
For those runners not qualifying on teams, individual at-large berths will be at stake on Saturday, as well. Menlo School senior Sam Parker seems a good bet to advance in Division IV after winning his first WBAL individual title last week while helping the Knights successfully defend their team title.
"This was more so for the team," Parker said of his first title. "We've been focusing on this and weren't going to settle for anything less. This is a great confidence boost for CCS. Hopefully we can take this momentum and ride it into (this) week."
The Menlo boys finished 1-2-9-10-17 to win easily with 39 points, but will find the CCS competition to be much tougher.
Still, the WBAL title was a good one as freshman Matt Myers, senior Lowry Yankwich, sophomore Andrew Schmitt and sophomore Michael Machlin followed Parker to the finish line.
"Just awesome," said Menlo coach Donoson FitzGerald. "It's a great group of guys, really self-motivated. This is what they had their eyes on. Last year was kind of a surprise (winning)."
Menlo was the heavy favorite after winning the three WBAL meets leading to the finals.
"They're talented, but they've worked hard," said FitzGerald, who returned four runners from last season and picked up freshman Myers, who quickly became the team's No. 2 runner.
The Sacred Heart Prep girls, meanwhile, won their first WBAL team title and hope to finish among the top three at CCS. One year ago, the SHP girls finished ninth in the league meet.
Freshman Meghan Holland led the Gators with a sixth-place finish of 19:51. Sophomore Kathryn Leahy was ninth (20:50), senior Elly Jones 10th (20:52), sophomore Courtney Schrier was 13th (20:57) and senior Riley Perdue 14th (20:58).
The second-place Menlo girls, meanwhile, were led by freshman Maddy Price, who finished third in 19:32 as the fastest freshman on the day. Junior Maddie Taylor was 11th (20:52) and her twin, Annie, was 15th (21:03). Brianna Quincy led the Pinewood girls with a 23rd-place finish of 22:00.