In 2005, the team made its first playoff appearance and went on to defeat the Newport Beach Breakers in the WTT Final to win its first King Trophy.

[8] After five years away from WTT having last played with the Kansas City Explorers in 1996, John McEnroe also made a few appearances with his younger brother's team.

[2] After two years in East Quogue, the Hamptons moved their home matches to the Amagansett-East Side Tennis Club in Amagansett, New York.

[2] John and Patrick McEnroe both returned to the court in 2003, for the Sportimes and were joined by Julia Vakulenko, Ellis Ferreira and Bea Bielik who were selected in the roster draft.

Following their difficult 2004 season, the Sportimes had the first choice in the 2005 marquee player draft and used it to select John McEnroe who returned to the team after a one-year absence.

The Sportimes made the first playoff appearance in franchise history on September 16, 2005, in the Eastern Conference Championship Match against the Boston Lobsters in Citrus Heights, California.

The Breakers jumped out to an early led when Devin Bowen and Ramón Delgado beat Jeff Morrison and Rajeev Ram, 5–2, in men's doubles.

Hingis then teamed with Jenny Hopkins to top Bondarenko and Rodionova in women's doubles, 5–2, to give the Sportimes a 17–10 lead going to the final set.

The team selected husband and wife Alex Bogomolov Jr. and Ashley Harkleroad as well as John Paul Fruterro and Vladka Uhlířová in the roster draft.

With WTT's 2006 conference championships decided based on regular-season records, the Sportimes' mark of 10 wins and 4 losses gave them the title over the second-place Philadelphia Freedoms, who finished 8–6.

Bogomolov and David Martin topped Crabb and Daniel Nestor in men's doubles, 5–3, to send the match to overtime with the Freedoms leading, 22–17.

In a highly competitive Eastern Conference, the Sportimes finished with 6 wins and 8 losses, only 2 matches behind the first-place New York Buzz, but out of playoff contention.

On the bright side, Witten was named WTT Male Rookie of the Year, the second consecutive season a Sportimes player had won the award.

Nathan Healey and Yaroslava Shvedova opened the match with a 5–3 set win against John McEnroe and Hana Šromová in mixed doubles.

Gabriela Navrátilová and Shvedova needed a tiebreaker to beat Harkleroad and Šromová, 5–4, and give the Buzz a 20–11 lead heading to the final set.

McEnroe and Witten won a tiebreaker over Patrick Briaud and Healy in the men's doubles to force overtime with the Buzz leading 24–16.

[2] John McEnroe, Jesse Witten and Ashley Harkleroad (who gave birth on the day of the draft and was picked in the third round) all returned from the previous season's squad.

Rennae Stubbs and Puchkova followed with a 5–2 women's doubles set win over Spears and Christina Fusano to put the Kastles in front, 17–14.

[20] John McEnroe, Robert Kendrick, Jesse Witten, Abigail Spears and Ashley Harkleroad all returned to the Sportimes for the 2010 season.

In the final set, Butorac and Kops-Jones beat Kendrick and Spears in mixed doubles, 5–2, to send the match to overtime with the Sportimes leading, 21–16.

Jarka Groth and Květa Peschke sealed the match with a 5–3 women's doubles set win against Ashley Harkleroad and Spears, and the Explorers registered a 21–18 victory to capture their first King Trophy.

The Sportimes had 7 wins and 7 losses and finished third in the Eastern Conference, narrowly missing qualifying for the playoffs by losing a standings tiebreaker to the Boston Lobsters.

Shortly before the start of the season, the Sportimes were informed of a scheduling conflict at SEFCU Arena which forced the team to move its two matches in the Capital District to McDonough Sports Complex on the campus of Hudson Valley Community College in Troy, New York.

[30] The Sportimes and Kastles met at the Family Circle Tennis Center in Charleston, South Carolina, a predetermined neutral site that hosted WTT Championship Weekend.

The Kastles jumped out to an early lead in the match as Leander Paes and WTT Male Most Valuable Player Bobby Reynolds won the opening set of men's doubles, 5–2, against Robert Kendrick and John McEnroe.

Květa Peschke and Kendrick struck back for the Sportimes with a 5–2 set win over Venus Williams and Leander Paes to tie the match, 7–7.

Williams dominated that final set of women's singles beating Harkleroad, 5–1, to give the Kastles a 19–15 victory and the Eastern Conference Championship and end the season for the Sportimes.

[35] After a temporary one-year absence during which it played its Capital District home matches in Troy, New York, the Sportimes returned to SEFCU Arena in Guilderland.

The team reversed what it had done during the first two seasons after the merger with the Buzz by playing five of its home matches in the Capital District and only two at Sportime Stadium at Randall's Island in New York City.

I am very glad to have found a motivated and able new owner for the franchise: a person who will be able to re-imagine it in another great tennis town – but I will miss my team.