Heartbreaks Since 1999: Top 10 Browns Losses Since the Rebirth of the Franchise

4. Nov. 4, 2001: Bears 27, Browns 21 (OT)

After winning just five games in the two previous years, the Browns were 4-2 under first-year coach Butch Davis heading into this showdown at Soldier Field. And, a 25-yard fumble recovery by former No. 1 overall pick Courtney Brown just 55 seconds into the game gave the Browns an early 7-0 lead. A 55-yard touchdown pass from Couch to Kevin Johnson late in the third quarter gave the Browns a 21-7 lead, and, with less than a minute remaining, that lead appeared to be safe. But that’s when things got really weird. Bears quarterback Shane Matthews, the regular backup, found Marty Booker on a 9-yard touchdown pass with 28 seconds left to cut the deficit to 21-14. Then, Chicago recovered an onside kick at the Browns 47. After two short completions, Matthews flung a Hail Mary pass that was tipped in the air and caught in the back of the end zone by running back James Allen for a stunning 34-yard touchdown with no time remaining. Then, before anyone realized what was truly happening, the game was over. After the Browns stopped the Bears in overtime, a Couch pass on their third offensive play was batted at the line of scrimmage and intercepted by safety Mike Brown, who returned the gift 23 yards for a game-winning touchdown.

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