Divisional Round, 1986: Cleveland 23 New York Jets 20

Thirty-eight-year-old Browns kicker Mark Moseley, a former Washington Redskin whom Cleveland had talked out of retirement in order to replace the injured Matt Bahr less than two months earlier, made the game-winning 27-yard field goal after 2:02 elapsed of the second overtime period, making this the third longest game in NFL history and giving Cleveland their first postseason win since 1969.

After Mosely missed a 46-yard field goal attempt on Cleveland's opening possession, the Jets scored first on their third drive of the game with an 82-yard drive. Quarterback Pat Ryan started it off with a 28-yard completion to Al Toon and finished it with a 42-yard touchdown pass to wide receiver Wesley Walker on a flea flicker play. Cleveland responded with Kosar completing passes to Ozzie Newsome for gains of 21 and 23 yards as he led the team 98 yards to score on his 37-yard completion to running back Herman Fontenot. Midway through the second quarter, Jeff Gossett's 39-yard punt pinned New York back on their own 4-yard line. The Jets were unable to get a first down with their drive, and to make matters worse, a 3rd down sack on Ryan by a gang of Browns defenders knocked him out of the game. New York's punt gave Cleveland on the ball at midfield, and they were able to take advantage of the field position, as Kosar's 25-yard completion to fullback Kevin Mack set up a 38-yard Mosely field goal that gave the Browns a 10–7 lead. The Jets, now led by Ken O'Brien, responded with less than two minutes left in the half on a last-second field goal drive to tie the game, featuring his season-long 16-yard run on fourth down and four to keep the drive alive.

Cleveland had to punt on the opening drive of the third quarter, and Kurt Sohn gave the Jets great field position with a 9-yard return to the Browns 41-yard line. New York then drove to a 37-yard Pat Leahy field goal to break the tie. Cleveland responded with a drive to the Jets 26-yard line, but it ended with no points on another missed field goal attempt by Moseley. Early in the fourth quarter, the Browns drove all the way to the New York 3-yard line, only to come up empty when Russell Carter intercepted a pass from Kosar in the end zone. Then after a punt, Kosar's next pass attempt was intercepted again, this time by Jerry Holmes, which set up Freeman McNeil's 25-yard touchdown run on the next play to give his team a 20–10 lead with 4:14 left in regulation. This led Jets announcer Charley Steiner to prematurely declare, "The Jets are gonna win this football game!"

But the Browns then drove 68-yards to score on Mack's 1-yard touchdown run with 1:57 left on the clock, on a drive that was aided by a roughing the passer penalty on Mark Gastineau that nullified an incompletion on second down and 24 from Cleveland's 18-yard line. After a failed onside kick attempt, the Browns stopped New York on two consecutive runs and then sacked O'Brien on a quarterback draw, bringing up 4th down on the Browns 48-yard line. Then they got another lucky break when a punt that would have pinned them inside their own 10-yard line was called back by a Jets holding penalty. On the second punt, Gerald McNeil returned the ball 10 yards to the Browns 32 with 53 seconds on the clock and no timeouts left. Following a 26-yard pass interference penalty on Carl Howard, Kosar completed a 37-yard pass to wide receiver Webster Slaughter on the Jets 5-yard line with 37 seconds to go. However, the Browns hurt themselves with excessive celebration after the catch, costing them several seconds before Kosar could break them up and get his team back to the line of scrimmage. The clock ran down to 15 seconds before the next snap, in which Kosar threw a pass that was broken up and nearly intercepted by Carter. Now with 11 seconds and no timeouts remaining, the Browns decided to play for overtime and had Moseley kick a game-tying 22-yard field goal.

After forcing the Jets to punt on the opening drive of overtime, Cleveland had a great chance to win after Kosar's 35-yard completion to Reggie Langhorne landed them at the Jets 5-yard line. They attempted a field goal on first down, but Moseley missed the 23-yard attempt. Still their defense continued to hold down New York, forcing them to punt on two more possessions. After the first punt, disaster nearly struck Cleveland when Mack fumbled the ball near his own 40-yard line, but Browns guard Paul Farren recovered it. With 2:38 left in the first overtime period, Cleveland got the ball on their own 31 following Dave Jennings' playoff record 14th punt of the game. After moving the ball to the Jets 42, receiver Brian Brennan made a key play when he broke up an errant pass that was nearly intercepted by Lester Lyles. This turned out to be crucial as the Browns running game would go on to take total control of the drive. First, Fontenot rushed for seven yards and then Mack added 26 yards on his next three carries, moving the ball to the 9-yard line to set up Moseley's second game-winning field goal attempt. This time, his kick was good, winning the game for the Browns after 17:02 of overtime play on an 11-play, 59-yard drive.

Kosar set postseason records for completions (33), attempts (64), and passing yards (483), but threw only one touchdown pass and two interceptions. Newsome caught six passes for 114 yards. Mack rushed 20 times for 63 yards and a touchdown, while also catching 5 passes for 51 yards. Toon was the Jets leading receiver with 5 receptions for 93 yards. The Browns tied a playoff record by recording nine sacks in the game, three by defensive tackle Carl Hairston. Cleveland finished the game with 558 yards of total offense. 45 of the Browns' 75 rushing yards in the game were gained on their final drive.

The game was featured as one of the NFL's Greatest Games as the Marathon by the Lake.

This was the first postseason meeting between the Jets and Browns.

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