1999 looked like it could finally be the year Stratford High broke through and won a SWC championship. They had garnered 91 points in finishing 2nd the previous year, and returned almost everyone from that team, as well as a large contingent of newcomers. A large number of seniors were also on the team to provide leadership for Coach Dirk Rozarie in his last season at SHS.1999 instead ended up both as a beginning and an end. Injuries crippled All-Stater Gene Fernandes and hurdler/pole vautler Frandoo Jean, who normally would have provided 1st place finishes in multiple events. Defections by many other team members brought the membership down from 40 at the start of the season to around 18 by the close of a disappointing 8-10 campaign and embarassing SWC finish. Stratford avoided finishing last solely because of senior Marvin Lawson, who demolished the 100 (11.46) and 200 (23.41). Brian Hamilton (5th in a strong javelin field at 146'10") earned the only other points.There were bright spots however. Lawson anchored the 4x100 team and regularly won the 100, 200 and 400. He also set the team record in the 200m (22.6). Jason Staples provided leadership and versatility in the face of adversity, mentoring the distance runners while running, at various times, the 800, 1600, 3200, 4x800, 5000, and 4x100. Warren Ross and Franco Jean stepped in at hurdles and formed a developing tandem. Harry Bridgeforth emerged as a force on the 4x800 team as well as a sprinter and hurdler. Seniors such as Bobby Cervone and Ade Taju-Deen helped out in the 4x100 and jumps, but it was not enough in the end to prevent a subpar season.
The future showed some promise however, with the return of Ross, Franco Jean, Bridgeforth, distance runner James daSilva, throwers Eric Loux and Tim Jacques. Loux also managed to gain All-State for his 5th place finish in the hammer throw after the regular season.