1989: Clive Charles, named Portland’s ­director of soccer, takes over as head women’s coach and leads the Pilots to a 10-6-0 season.

1990: Harry A. Merlo Field, one of the ­nation’s best soccer facilities, opens for play and Tiffeny Milbrett begins an illustrious career on The Bluff. The Pilots win the first of two straight Northwest Collegiate Soccer Conference Championships and appear in the national top 20 for the first time, reaching No. 12. Milbrett is named the NCSC Player of the Year and is the Soccer America Freshman of the Year.

1991: The women’s program, 13-2-2, makes a strong case for its first-ever NCAA playoff berth, but will have to wait a year. Milbrett rakes in All-America honors and her second NCSC Player of the Year award while establishing a school record with 25 goals.

1992: Charles pulls off a rare coaching feat, leading two teams to the NCAA playoffs in the same year. The women’s side makes history, winning a school-record 18 games and earning the University’s first women’s NCAA playoff berth and the first of seven consecutive postseason bids. Charles leads his men to a No. 1 national ranking and the women to a No. 3 rating. The women join the WCC and both programs claim league championships. A crowd of 5,596, then the largest in U.S. women’s soccer history, jammed Merlo Field to witness a first-ever meeting between Portland and top-ranked North Carolina. Tiffeny Milbrett scores 30 goals and adds 12 assists to set UP’s single-season points record of 72.

1993: The Pilot women’s and men’s sides simultaneously earn NCAA playoff berths for the second consecutive year. With Tiffeny Milbrett shelved due to injury, Shannon MacMillan and freshman sensation Justi Baumgardt lead the Pilots to their first-ever NCAA win, a 2-0 first round defeat of conference rival Santa Clara. Portland loses in the quarterfinals at Stanford by a 1-0 tally. Charles is named head coach of the U.S. U-20 Women’s National Team.

1994: The Pilot women recapture the WCC title with a 7-0-0 record and reach the NCAA Final Four, staged at Portland’s own Merlo Field. The highly-successful, but injury-plagued season comes to an end with a 1-0 loss to Notre Dame. Tiffeny Milbrett and Shannon MacMillan are each finalists for the Missouri Athletic Club Player of the Year and Hermann Trophy honors, while the Pilots place a record five players on the all-WCC first team.

1995: Charles leads both programs to their respective Final Fours, becoming only the second collegiate soccer coach in history to lead two teams to the NCAA semifinals in the same year. The women’s side lost 1-0 in overtime to Notre Dame in the national championship game, finishing the year with a school-record 20 wins. Shannon MacMillan is named the Missouri Athletic Club’s player of the year and presented the Hermann Trophy.

1996: The Pilot women reach their third straight NCAA Final Four, but are turned away, 3-2 by No. 1 Notre Dame in the semifinals. Portland finishes the season with 19 wins and a third consecutive WCC title. Cheryl Loveless established a school record and ranked second nationally with a 0.42 GAA, and third with 13 shutouts. Justi Baumgardt becomes the fifth consecutive Pilot to garner WCC Player of the Year honors after guiding UP to its second undefeated conference season.

1997: Senior Justi Baumgardt earns her fourth all-WCC first team honor, becoming just the fourth female WCC player to accomplish that feat. Baumgardt leaves as UP’s all-time assists leader (50), and third-leading scorer. She leads the Pilots to a fourth straight WCC title and sixth straight NCAA appearance, but a first-round loss at home to UCLA ends a 14-5-0 season. The UP women rank second nationally in home attendance average (1,834).

1998: Despite a roster depleted by injuries, the Pilot women advance to their fourth NCAA semifinal in five years, but lose 1-0 in four overtimes to No. 1 North Carolina in what would be the longest game in playoff history. Portland has a 19-3-2 final record. Angela Harrison sets a new school record with a 0.30 GAA, and senior defender Michelle French is a consensus All-America pick. Early in the season, head coach Clive Charles earns his 300th career win, making him just the 11th coach in NCAA history to amass that many wins.

1999: The Pilots finish with a 12-7-1 record, but still tied for second in the WCC. Portland misses its first NCAA tournament in eight seasons, losing to five eventual tourney teams. Seven players earn all-WCC honors, topped by first-teamers Susanna Heikari and Erin Misaki.

2000: The Pilots, unheralded as the season begins, advance to their fifth NCAA semifinal in seven years, only to lose 1-0 to UCLA. Portland finishes with an 18-4-0 record and wins the WCC title with a 6-1-0 record. Sophomores Erin Misaki and Lauren Orlandos earn several All-America honors, while Misaki is the WCC Co-Player of the Year, and Orlandos is WCC Defender of the Year as the Pilots post 15 shutouts.

2001: Portland rambles through the NCAA Playoffs, winning its first four games by a 15-1 margin, before falling 2-1 to North Carolina in the semifinals. The Pilots tie a school record with 20 wins (20-4-0), and tie for second in the WCC at 5-2-0. Freshman scoring sensation Christine Sinclair is named the national freshman of the year, and is joined on several All-America teams by junior defender Lauren Orlandos.

2002: The Pilots made history recording the school’s first-ever National Championship by defeating Santa Clara 2-1 in double overtime in the College Cup Final. Portland finishes the year 19-4-3 and sophomore striker Christine Sinclair is recognized as one of the premier collegiate soccer athletes, leading the nation with 26 goals. Sinclair is named the WCC Player of the Year, wins the Honda Award for the best woman’s collegiate soccer player, and is joined on various All-America teams by senior defender Lauren Orlandos. Midfielder Lindsey Huie is named the WCC Freshman of the Year and a first team Soccer America Freshman All-American.

2003: With Christine Sinclair redshirting to compete at the World Cup, the Pilots rely heavily on a strong freshman class. Seven newcomers see regular action and at least five start every match. The Pilots advance to the third round of the NCAA Tournament before falling to rival Santa Clara in a shootout after a scoreless tie. Portland finishes with a 18-3-2 overall record. All-American midfielder Lindsey Huie scores 12 goals and adds 13 assists. Freshman defender Stephanie Lopez is named a Soccer America Freshman All-American and is one of eight Pilots to earn all-WCC honors. Senior Imani Dorsey claims WCC Defensive Player of the Year honors and her fourth straight all-WCC selection.

2004: Stephanie Lopez, Angie Woznuk and Megan Rapinoe are summoned for national team duty and forced to redshirt, but with the return of Christine Sinclair Portland ties a school record with 20 wins and earns its 12th NCAA playoff berth. Sinclair is honored with the Missouri Athletic Club’s Hermann Trophy presented to college soccer’s top player, joining Shannon MacMillan (1995) as the only Pilots ever to receive the honor. Lights are installed at Merlo Field and The Clive Charles Soccer Complex allowing night games to be played for the first time in school history. A crowd of 4,070 show up at the inaugural night match, a 4-0 victory over Weber State on Sept. 10.