The team was founded by a group led by venture capitalist and entrepreneur Mark Ein, a resident of the Washington metropolitan area.
[3] In the Roster Player Draft on April 1, 2008, the Kastles selected Justin Gimelstob, Sacha Jones, Scott Oudsema and Mashona Washington.
[4] At a press conference on April 30, 2008, that included Kastles owner Mark Ein, WTT CEO/commissioner Ilana Kloss, WTT co-founder Billie Jean King and Washington mayor Adrian Fenty, the Kastles announced plans for the construction of a temporary 2,020-seat stadium on the parking lot on which CityCenterDC was expected to be built in the future.
"[5][6][7] The team announced that season tickets as well as three-match packages that included the inaugural home match in which Serena Williams was scheduled to appear and visits by John McEnroe and the New York Sportimes and by Anna Kournikova and the St. Louis Aces were on sale.
The Kastles planned to give away more than 1,000 tennis racquets to local children attending their matches and at community clinics sponsored by the team.
Looking ahead to his upcoming meeting on the court with Kournikova in mixed doubles, Gimelstob said that he wanted to hit her hard in the midriff when serving in her direction.
[10] The Kastles met the Philadelphia Freedoms in their inaugural match on July 4, 2008, at the King of Prussia mall in Upper Merion Township, Pennsylvania.
[11] The following day, the Kastles signed Tripp Phillips as a substitute player to fill in for Justin Gimelstob for their match in Delaware that evening.
Washington paired with Sacha Jones to take the fourth set of women's doubles in a tiebreaker that gave the Kastles an 18–14 lead.
After Oudsema dropped the final set of men's singles to cut the Kastles' lead to 20–19, he won the first game of overtime to clinch a 21–19 triumph over the Delaware Smash.
The team conducted a youth tennis clinic at Kastles Stadium, and Serena Williams, fresh off a loss in the Wimbledon Ladies' Final to her sister, Venus, and a transatlantic flight arrived about an hour late.
[15] Kastles owner Mark Ein joined the sellout crowd, taking his courtside seat, flanked by Washington mayor Adrian Fenty and WTT co-founder Billie Jean King, prepared to watch his undefeated team.
In the opening set of men's doubles, Amir Hadad and Jan-Michael Gambill thumped Scott Oudsema and Justin Gimelstob, who was making his season debut, 5–1.
Williams converted a break point in the sixth game and won the closing set of women's singles, 5–2, over Marie-Ève Pelletier to send the match to overtime with the Lobsters leading, 21–17.
[16] On the day of their home opener, the Kastles announced they had signed Robby Ginepri as a substitute player to fill in for Gimelstob on July 11, 2008.
Ginepri completed the dramatic comeback by taking the super tiebreaker, 7–4, to give the Kastles their first home victory in franchise history.
[18] The following day, the Kastles announced they had signed Kevin Kim as a substitute player to replace Justin Gimelstob in their July 13 match at Newport Beach.
Delgado entered the match leading WTT in men's singles winning percentage having taken 31 of 47 games played and had not yet dropped a set in the event all season.