WINCHESTER — When reflecting on the greatest games of the last decade for the Winchester High football team, head coach Wally Dembowski (who took over in 2011) and his staff focused on wins that were the building blocks to where the Sachems are now, in good shape while moving forward to the 2020 season.

Winchester 21, Woburn 19 OT (2013) — The “quickest overtime game in history” as the Sachems upset the heavily-favored Tanners, at Knowlton Stadium, on a cold, sunny Thanksgiving Day.

The game was tied 7-7 going into the fourth quarter when Turkey Day hero Timmy O’Brien put Winchester ahead with a 36-yard touchdown run. Woburn quarterback Rob Voci put the Tanners on his shoulders, driving his team with a mixture of runs and passes before finding Marvin Jean for the tying score. Both teams missed their conversion attempts, sending the game into overtime for the first in the history of the rivalry (overtime went into effect in 2002).

Woburn had the ball first in OT and scored on the initial play, only to have O’Brien, who also had two interceptions, knock down Voci’s conversion pass attempt.

Sachems’ quarterback Michael Grassey, who threw to Pat Gill for Winchester’s first touchdown, found John Dooley on the home team’s first play of overtime. Grassey then hit Gill for the deciding points in the triumph.

Winchester 14, Reading 7 (2017) — While the game itself was not particularly impressive — the Rockets’ skill positions were ravaged by injuries that year — this may have been the biggest psychological Sachem triumph of the decade. Not only was it the first win over the Rockets since Dembowski took over (and back to 2007), but it also came as the Winchester High renovations were on the verge of being completed.

“A huge win at home that gave our program confidence we could compete with the benchmark programs,” said Dembowski. “It was our last year in construction and we’d have a new locker room, weight room, meeting rooms and a practice facility with lights in 2018. The game has led to (Winchester’s first) back-to-back winning seasons in almost two decades.”

As for the game, quarterback Liam Fitzpatrick made only his third start of the season (in Week 7) and he threw two touchdown passes to his favorite target, wide receiver Evan Clarke, who had 6 catches for 105 yards. In addition to Fitzpatrick’s 120 yards passing, he also rushed for 134 yards on 18 carries while running back Peter Gallagher ran for 101 yards on 29 carries.

It was a scoreless game until Reading’s John DiMare found a hole and went 68 yards for a touchdown in the second quarter. Fitzpatrick tied the game on Winchester’s next drive with a 50-yard pass to Clarke.

Even though the defense held the Rockets to 70 yards of total offense besides the DiMare touchdown, the Sachems finally went ahead to stay on another touchdown pass with 3:02 left.

Winchester 27, Woburn 21, 2 OT (2018) — Tommy Degnan made himself a Thanksgiving Day folk hero, coming off the pine on a 15-degree morning to score four touchdowns and 26 of Winchester’s 27 points as a running quarterback.

The game went back and forth with the Tanners having the first chance to put the game away, when they had the ball in Sachem territory with a 15-7 lead.

The Winchester defense came up with a strip sack and the fumble recovery was turned into a potential tying touchdown for Degnan. Starting quarterback Tony Fiorentino hit Degnan with the two-point conversion pass to tie the score at 15-15. Woburn had a chance to take the lead in the final minute but its 35-yard field goal attempt fell short.

Both teams scored on their first possession of overtime, but both came up short on their mandatory two-point conversion tries.

The Tanners had the ball first in the second overtime and were unable to score, thanks to a defensive effort led by defensive end Joe Lepore. It took the Sachems all four downs before Degnan won the game with a 1-yard run to daylight.

Winchester 28, Lynn Classical 22 (2019) — The first playoff win in new era for the Sachems, who were hosting the first round game for the second year in a row. Winchester had gotten hammered in their previous two playoff games versus teams from the Northeastern Conference, including that previous home game against Beverly, so this victory was huge on more than one front.

Running back Jimmy Gibbons was the star of this game, scoring three touchdowns on 108 hard-earned yards. In fact, his 34-yard touchdown run in the fourth quarter, that gave the Sachems a 28-15 lead, represented more than a third of his rushing total.

Tommy Degnan at quarterback also rushed for over 100 yards (10-117) and threw a touchdown pass to wide receiver Henry Kraft.

Degnan set the tone for Winchester with a 59-yard run on the first play of the game for the Sachems, and Gibbons scored from the 9 on the next play. Winchester took a 7-6 lead with Mario Caloiero’s extra point and the game would switch back and forth until the Sachems took a 22-15 halftime lead on Kraft’s touchdown reception.

Winchester got its final touchdown, early in the fourth quarter, capitalizing on an interception by cornerback Jakob Flores. The Rams made it interesting with a touchdown with 8:11 left, but the Sachem offense ate up five minutes of clock and Degnan closed out Lynn Classical’s last drive with an interception.

Winchester 42, Danvers 27 (2019) — The biggest win of the decade had the Sachems knocking off the No. 1 seed in MIAA Div. 3 North, while earning them a spot in sectional final.

The heavily-favored Falcons easily scored on their first two drives to take a 14-7 lead before Winchester’s defense shut down their ground attack, and the offense went on a 21-0 run to give the Sachems a 28-14 lead in the third quarter.

Danvers got to within a touchdown twice before Degnan clinched the victory with a 37-yard run with 34 seconds left. It was his third rushing touchdown while Gibbons had two touchdown runs. Degnan rushed for 124 yards and threw for 147 and one touchdown.

Winchester 21, Melrose 14 (2012) — The Sachems upset the powerful Red Raiders (who went 8-3 that year) in Dembowski’s second year at the helm. It was highlighted by quarterback Tim Mangano’s eight-yard touchdown scramble at the end of the third quarter which put Winchester ahead to stay, and a defensive stand in the fourth quarter that culminated with defensive back George Casey knocking down Melrose’s attempt for a go-ahead score on a fourth-and-goal, with less than a minute to play.

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