Wrentham started the 1999 year with high expectations, after having lost the 1998 conference championship game to Monterey Bay in overtime. The 1999 season started in Monterey Bay. This time, Wrentham was able to defeat the Sea Lions, 35-24. The next week, Wrentham played Alabama. Alabama was able to run for 274 yards and won the game 28-15. Wrentham rebounded from their loss with easy victories over California, Long Island, and Moffat. In week 7, at 5-1, Wrentham faced the HTFL Champion HTFL Tsunami. Wrentham held a 17-14 lead with 10 minutes left in the game, but Hawaii was able to drive down field and win the game 21-17. The next week, Wrentham lost to division rival Fort Bragg, 21-7. Wrentham's record had now dropped to 5-3. However, that would be Wrentham's last loss of the season. Wrentham defeated Rancho Bernardo the next two weeks before playing Fort Bragg again. Wrentham came out with a win by a safety, 32-30. The next week Wrentham beat division rival Long Island 29-6. Wrentham finished out the regular season by defeating Frankfurt and Tucson. Wrentham won the Colonial Division, but Alabama got homefield advantage for the playoffs.
Wrentham started the playoffs at home against Fort Bragg, a team that they split their games with during the regular season. Wrentham defeated the Rangers 34-16. In the VLC Championship game, Wrentham played Alabama. Barry Sanders and Herman Moore both had big games, as did Bracey Walker, who returned a punt 77 yards. Wrentham's defense was spectacular, and the Rocketeers won 48-11. Wrentham hosted the World Bowl against Hawaii 2 weeks later. Wrentham was killed by turnovers, throwing 2 interceptions and losing 1 fumble. Wrentham recovered 3 other fumbles. In total, 5 Wrentham drives were ended by turnovers or by fumbles. Wrentham lost 42-19.
This was a great year for the Wrentham Rocketeers. Barry Sanders broke the season rushing record with 1708 yards. Herman Moore was amazing as usual, with 79 catches for 1155 yards. Keith Sims, a newcomer to the team this year, proved himself to be a spectacular offensive lineman. On defense, Wrentham's new defensive line of Culpepper, Dotson, Wheeler, and DeVries proved itself. In the defensive backfield, Fred Thomas and Bracey Walker shined as great cornerbacks and punt returners. Andre Cooper, another newcomer to this year's team, was the strong safety, and led the team with 3 interceptions. Next year Wrentham will maintain the same goal as always, to win the HTFL Championship.
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