For their inaugural season, the Skyhawks hired Brian Drahman, who had been the pitching coach for the New Jersey Jackals, as their manager.

Due to poor weather and other factors, the Skyhawks attendance was disappointing early in the inaugural 2006 season,[1] until the team found itself in a tight, multi-team race for the first-half pennant.

The Skyhawks' 2007 season started poorly; they lost 10 of their first 11 games including a sweep at the hands of the traveling Grays franchise.

By the final weekend of the first half, the Skyhawks were 25–19, just three games back of the first-place Québec Capitales—who were in Skylands Park for a four-game series.

In a similar ending to 2006's first half, however, the Capitales won three of four, and Sussex had to settle for a three-way third place tie with their sister team the Jackals and the Atlantic City Surf.

In the league semifinals against Worcester, the Skyhawks dropped the opener of the best-of-five series, 3–2, before roaring back to win three in a row.

In Game 4, Worcester jumped to a 5–0 lead before Sussex scored six runs in the fourth en route to an 8–5 win, and a berth in the Can-Am League Championship Series against Quebec.

Finally, in the bottom of the tenth, Jorge Moreno's single scored Michael Perodin to give the Skyhawks a 3–2 win.

In the second game, Sussex scored four runs in the first inning, then watched Quebec come back to take a 5–4 lead.

The lead seesawed back and forth until Matt Weston's two-RBI single in the eighth sealed the Skyhawks' 8–6 win.

On September 12, 2008, the Skyhawks met Les Capitales Stade Municipal in Quebec, looking for an improbable sweep in the Championship Series.

In game three, the Skyhawks offense bludgeoned the Caps pitchers in the early going, plating ten runs in the first four innings and cruising to a 10–5 win, becoming the first championship team to play in Skylands Park since the New Jersey Cardinals won a New York–Penn League title in their inaugural season in 1994.

Featuring nine players from the prior year's championship team, the Skyhawks got off to a 4–1 start, taking three of four on the road against the Brockton Rox, then won their home opener, 4–3, against Worcester.

But a slump during which Sussex lost seven of eight games dropped the Skyhawks below .500, and they never recovered, ending the first half of the season at 21–26, tied for last place in the Can-Am League.