The Cavaliers wrapped up the Blue Hen Conference Flight B championship and automatic Division II state tournament berth behind Brandon Brown's 141 yards and 2 touchdowns rushing. The Cavs overcame a 12-7 first half deficit with 21 unanswered points to finish the regular season at 8-2 overall and 5-0 in Flight B. Quarterback Matt Keen went 3-for-4 for 91 yards including a 10-yard TD pass to Dave Woods. Brown scored on runs of 5 and 4 yards and J.C. Morgan on a run of 10 yards.

The Cavaliers recorded their fourth shutout of the season to rise to 4-0 in Flight B and 7-2 overall. Senior running back Brandon Brown scored on runs of 3 and 5 yards and fullback J.C. Morgan caught a 4-yard touchdown pass from quarterback Matt Keen.

Middletown put seven different players in the end zone and the defense recorded three interceptions and three fumble recoveries. In rising to 6-2 overall, the Cavaliers scored the game's first 48 points, including 10- and 33-yard touchdown runs by J.C. Morgan, a 3-yard touchdown run by Brandon Brown, and TD passes of 7 and 70 yards from Matt Keen to Mike Woods and R.C. Cleveland, respectively. Shawn Tolson scored on a 60-yard return of a fumble recovery.

Middletown rose to 2-0 in Flight B and 5-2 overall with the Homecoming rout. Senior running back Brandon Brown rushed for 148 yards and two touchdowns. Brown had been hampered by a hamstring injury in the previous three games. The Cavaliers rushed for 350 yards including 86 by fullback J.C. Morgan, who scored on a 35-yard TD run. The defense held Concord to just 66 total yards.

Middletown lost to the Auks this time in a rematch of the 1998 Division II state championship game. The Cavaliers scored on a 1-yard touchdown run by Joe Salerno with 1:32 remaining to pull within 14-13, but were stopped cold by the Archmere defense after deciding to go for the two-point conversion instead of tying the game with an extra point kick. The Auks then recovered an onsides kick to give Middletown back-to-back losses for the first time since 1996. Quarterback Matt Keen scored the Cavs' other TD on a 1-yard run. Standout running back Brandon Brown missed the game with an injury.

The Cavaliers' 28-game winning streak was snapped when they failed to convert a two-point conversion attempt late in the game. The Cavs rebounded from a 14-0 halftime deficit to pull within 21-20 with 4:31 left on a 15-yard touchdown run by Ira Wilson, but instead of settling for an extra point kick to tie the game and possibly force overtime, Middletown tried for two points but was stopped a yard short of the goal line. A last-ditch drive with barely a minute left in the game resulted in an interception to halt the Cavaliers' streak. The Cavs also scored on a 1-yard run by Rausheen Lively and a 2-yard run by Brandon Brown.

No details are available on the victory over Hodgson that gave the Cavaliers their 28th consecutive victory and raised their 1999 record to 4-0.

The Cavaliers posted their 27th consecutive victory over a Delmar team they have beaten in the first round of the Division II state tournament the past two seasons. Six different players scored touchdowns for Middletown. J.C. Morgan started the scoring with a 33-yard run. Brandon Brown followed with an 85-yard TD run, Dave Woods caught a 26-yard touchdown pass from quarterback Matt Keen, Joe Salerno scored on a 3-yard run, Rausheen Lively scored from 15 yards out, and Shaun Raye added a 1-yard TD plunge.

Quarterback Matt Keen and running backs Brandon Brown and J.C. Morgan each scored touchdowns as the Cavaliers rose to 2-0. Brown rushed for 141 yards and scored on a 5-yard run for Middletown's final score in the third period. Morgan scored on a 30-yard run and Keen on a 7-yard run. The Cav defense registered 8 sacks including 5 by defensive end Derek Perry.

The Cavaliers started the season with a rout of their rivals from the Henlopen Conference Southern Division. Middletown scored on its first two plays from scrimmage to give a rude greeting to Jeff Weiner, a Cavalier assistant for the past 10 years who was making his debut as Smyrna's head coach. Middletown totalled 494 yards of offense. Senior running back Brandon Brown, the state's co-offensive player of the year in 1998, ran for 194 yards including touchdowns of 69 and 47 yards. Rausheen Lively added TD runs of 13 and 70 yards, fullback J.C. Morgan scored on runs of 32 and 5 yards, and a 7-yard run by quarterback Matt Keen.

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