Dudley didn't wait long to make an impact, converting the first overall pick at the 1999 NHL Entry Draft in Boston into five players ready to step in and three high draft future choices for an organization needing a boost in depth. Among the new players acquired in the deal were goaltender Dan Cloutier from the New York Rangers and defenseman Andrei Zyuzin from San Jose, two young players just beginning to realize their potential in the NHL. 

Dudley's next move was to bring in former Chicago Blackhawk and Buffalo Sabre Steve Ludzik as the head coach who would guide the team on the ice. The reshaping continued just before the season when Dudley added free agents Stan Drulia, Ian Herbers and Ben Clymer, and pulled off a steal with the acquisition of left wing Fredrik Modin from Toronto.

The roster turnover throughout the season would be great as Dudley molded a team that fit his criteria of size, speed and character. Important acquisitions that would occur before the end of the season would include: Gordie Dwyer from Montreal for Mike McBain; Todd Warriner from Toronto for a draft choice; Mike Johnson and Marek Posmyk and a pair of draft choices from Toronto for Darcy Tucker and a draft choice; Cory Sarich, Brian Holzinger, Wayne Primeau and a draft choice from Buffalo for Chris Gratton and a draft choice; Ryan Johnson and Dwayne Hay from Florida for Mike Sillinger.

On the ice the young Lightning showed distinct improvement at home, including a 6-1-2-2 stretch at the Ice Palace from mid-October to mid-December. Included in that stretch was a five-game home win streak with Detroit, Buffalo, Pittsburgh and Philadelphia among the victims. But as the youngest team in the league, the Lightning continued to struggle on the road and fell out of the playoff race in January.

Despite the on-ice struggles heads were not hanging at the Ice Palace, mostly due to the inspired play of 19-year-old center Vincent Lecavalier. In only his second full season, Lecavalier gave a a taste of the future with a 25-goal, 67-point season that included a four-point game at Florida on January 1 and several highlight-reel goals. Adding to his remarkable season was the choice by management to name Lecavalier captain on March 1 following the trade of Gratton, making him the youngest full-time captain in league history. Meanwhile, Modin was having a memorable season of his own, setting career highs with 22 goals and 26 assists in 80 games.