On December 27th of this year, the city of Cleveland will have gone forty two years since their last professional sports championship … a shocking 27-0 rout of the heavily favored Baltimore Colts in the 1964 NFL Championship Game.The Browns remained formidable throughout the late sixties, going to and losing three additional championship games after the ’65, ’68, and ’69 seasons. The team was poor throughout most of the seventies before returning to the playoffs in 1980 behind Brian Sipe, losing their first round playoff game to the Oakland Raiders on the infamous “Red Right 88” play. The team had a great run from 1986-1989, and then made just one more playoff appearance after the 1994 season before being stolen away by scumbag Art Modell after the 1995 season. The team has had six losing seasons out of seven since returning the league in 1999. The past forty two years were very unkind to our Indians as well ... until about twelve years ago. The team had just six winning seasons from the 1964-1993, winning zero division titles in the process. Upon moving to Jacobs Field in 1994, the Tribe rattled off eight winning years in a row, snaring six division titles and appearing in two World Series.And the Cavaliers didn’t arrive in town until 1970, but their 36-year history has stripped valuable years off the back end of the lives of diehard fans as well. They were miserable upon entering the league, nearly pulled of A Miracle In Richfield in ’76, then returned to obscurity before having several potential championship seasons stripped from them by Michael Jordan and the Chicago Bulls during the teams best stretch of play from 1988-1995. The team has once again ascended to the upper tier of the league as of late, thanks to the addition of LeBron James in 2003.Why open these old wounds? Because it’s important to remember our past, as torturous as it may be. It will only make the sweet taste of success that much greater when it arrives at The North Coast.Here they are, the ten most heartbreaking losses this city has suffered in the last twenty years, ranked in order of how badly they hurt.1. October 26th, 1997: Game 7 of the World Series - Florida Marlins 3 Cleveland Indians 2 (in 11 innings)It was the one Indians team none of us figured had a chance at the beginning of the playoffs. That was before thrilling playoff series wins vs. the Yankees and the Orioles, and we found ourselves up 2-1 heading into the bottom of the ninth inning of game 7 of the World Series. It was the year of Matt Williams and Marquis Grissom. The year Sandy Alomar Jr. could do no wrong, even winning the All-Star Game for the AL at the Jake with a dramatic home run.I’ll never forget how bad this one hurt. I lay collapsed on the ground of Scalpers Bar & Grill on Mayfield Rd for about 20-30 minutes afterwards, wondering what had happened. It was ours. We had it. I remember during the latter innings, trying to block from my mind the recurring thoughts of how I would celebrate, who I would call … not wanting to jinx mentally what seemingly would be the first pro sports title of my lifetime to celebrate. I had been waiting twenty years for this one.We all remember Jose Mesa allowing that run in the bottom of the ninth on a Craig Counsell sac fly that tied the game at two, and Renteria’s hit off Charlie Nagy in the bottom of the 11th to score the aforementioned Counsell. Many forget Miek Hargrove’s ballsy (and correct) call to start rookie Jaret Wright over Nagy. Add in the facts that we had guys on 1st and 3rd with one out in the top of the 9th ... and Tony Fernandez’s (.471 WS average) 11th inning error that allowed Renteria’s bases loaded two out heartbreaker, and losses just don't get any tougher than this one. The domination by Livian Hernandez, and even Chad Ogea. Manny’s 3-26 performance, and Justice’s 4-27 no-show. The closest this city has ever come to a championship in my lifetime. And the toughest loss I've ever had to endure.2. January 11th, 1987: AFC Championship Game - Denver Broncos 23 Cleveland Browns 20 (OT)It was Bernie’s 2nd year, a year in which he was the MVP of the AFC with over 4,000 yards passing, had the leagues lowest INT rate, and led the team to a 12-4 mark. Byner and Mack. The Schottenheimer “There’s a gleam man” pre-game speech and his tough as nails defense. The double overtime thriller over the Jets the week before. Just one home game away from our first Super Bowl appearance.All to be undone by a Rich Karlis field goal that may not have even been good. Made possible by a 98-yard drive by John Elway in which he converted an improbable 3rd and 18 from his own territory. I'd delve further into this game, but we've all seen it countless times on ESPN Classic.3. January 17th, 1988: AFC Championship Game - Denver Broncos 38 Cleveland Browns 33Just one year later, the Browns once again found themselves one game away from a shot at greatness, and once again matched up with the Broncos…this time at Mile High Field. The Browns had spanked Eric Dickerson and the Colts 38-21 in the previous round.The Browns fell behind 21-3 by halftime, then turned an early 3rd quarter Elway INT into a Kosar to Langhorne strike to make it 21-10. The teams exchanged quick scoring strikes before the Browns held, and Earnest Byner scored his second straight TD to bring the Browns to within 28-24. Karlis booted a FG, then Kosar hit Slaughter to tie the game at 31. The Broncos marched downfield again, this time on an Elway pass to Sammy Winder, making it 38-31. The Browns attacked right back, before Jeremiah Castille stripped Earnest Byner at the three-yard line on a run that would have ended in a game tying TD. The Broncos took a safety and won 38-33.4. October 28th, 1995: World Series Game Six - Atlanta Braves 1 Cleveland Indians 0After wallowing in the depths of sub-mediocrity for the previous forty seasons, the Indians returned to the post-season with a bang in 1995. They had the best record in baseball, won the AL Central by 30 games, and had both the best batting average and best ERA in the American League…finishing 100-44 in the lockout shortened ’95 season.They scored dramatic playoff series wins vs. the Red Sox and the Mariners, before running into the Atlanta Braves in the World Series. Their big bats were quieted by the dominant Braves trio of Glavine, Smoltz, and Wohlers…all ending in a one hit masterpiece 1-0 shutout at the hands of Glavine and Wohlers in game six. Tony Pena’s 6th inning single was the only Indian hit, and Dave Justice’s 6th inning solo HR off of Jim Poole was the difference. The Indians hit just .176 as a team against Braves pitching in the six game series loss.5. May 7th, 1989: Eastern Conference Playoffs Round One - Chicago Bulls 101 Cleveland Cavaliers 100The shot. The Cavaliers, off the heels of a 57-25 season and a Magic Johnson endorsement as The Next Big Thing in the NBA found themselves as the #3 seed thanks to the 62-20 Pistons being in their same division. They drew the up and coming #6 seeded Chicago Bulls and young phenom Michael Jordan, who would torture the franchise for many years to come. The Cavs had just won a thrilling 108-105 affair in Chicago in game four, and had Da Bulls back on their home court. Many forget the fabulous give and go inbounds pass by and back to Craig Ehlo that gave the Cavs a 100-99 lead with just seconds left.6. May 29th, 1992: Eastern Conference Finals Game Six - Chicago Bulls 99 Cleveland Cavaliers 941992 was a magical season for the Cavaliers as they once again reached 57 wins after two years of injury-plagued seasons since The Shot. Mark Price, Brad Daugherty, and Larry Nance all made and excelled in the All-Star game and Price had a memorable win in the 3-Point Shootout. The team tore through the Nets in the first round, and ended Larry Bird’s career with a thrilling seven game win over the Celtics in the second round before once again finding Jordan in their path. The Cavs won games two and four to tie the series at 1-1 and 2-2 respectively before getting pummeled 112-89 by the Bulls in game five in Chicago…a loss that seemed to take the steam from the Cavs in this disheartening game six loss at The Coliseum.The Cavs would go on to get again knocked out of the playoffs in both ’93 and ’94 by Jordan and the Bulls…both series ending in Bulls sweeps. The team lost 3-1 and 3-0 to the Knicks in the playoffs in ’95, and ’96…then lost to the Pacers in four games in the first round in 1998, and have not returned to the playoffs since.7. January 14th, 1990: AFC Championship Game - Denver Broncos 37 Cleveland Browns 21Another AFC Championship Game, another gut wrenching loss to the Broncos. Bud Carson had taken over for Marty. Lindy was gone. The team defeated the Bills 34-30 in a thriller to get to this one, only to fall behind 24-0 in a hurry. The team rallied to make it 24-21 before running out of steam and losing 37-21.8. January 5th, 2003: AFC Playoffs Wildcard Round - Pittsburgh Steelers 36 Cleveland Browns 33In the first return to the post-season Post Betrayal, the Browns found themselves matched up against the hated Steelers and without starting QB Tim Couch who broke his leg in a thrilling final week victory vs. the Falcons that secured the team a playoff spot. Career backup Kelly “The Messiah” Holcomb threw for 429 yards and 3 TD’s, overcoming a non-existent Browns running game. The Browns led 24-7, and were up 33-21 with just ten minutes left, but were unable to run the ball and control the clock … eventually coming apart at the seams defensively and surrendering three Tommy Maddox TD passes in the final nineteen minutes of play. A Dennis Northcutt drop with just over a couple of minutes left on 3rd down and 12 forced a Browns punt that the Steelers converted into a Fuamata-Maafala TD with 54 seconds left for the win.9. May 18th, 2006: Eastern Conference Semifinals Game Six - Detroit Pistons 84 Cleveland Cavaliers 82The Cavs came into this series with almost no expectations. The vibe around town was "try and get it to six games to gain some experience for next year". After getting pasted in games one and two at Detroit, the last few believers had given up hope.Then ... the upstart Cavaliers, in their first playoff appearance of the LeBron James Era, improbably took the next three games of the series, setting up an opportunity to knock the two time defending Eastern Conference champions out of the playoffs from the friendly confines of Quicken Loans Arena.The game was incredibly tight throughout. The Pistons hung on to emerge victorious thanks to nine fourth quarter offensive rebounds, including five in the final 1:39, as well as big final frames from Chauncey Billups and Rasheed Wallace. Billups and Wallace scored Detroit’s final thirteen points, and seventeen of their final nineteen. Nearly all of those points came on second and third chances, as the veteran laden Pistons kept narrowly beating the Cavaliers to loose balls and rebounds. The Cavs had held Detroit to just two offensive boards through three quarters.Predictably, the Cavs were pummeled in game seven back in Detroit, losing 79-61 in a game that was never close.10. October 11th, 1999: AL Playoffs Divisional Series - Boston Red Sox 12 Cleveland Indians 8After winning the first two games of the series, injuring Pedro Martinez and Nomar Garciaparra in the process, first round victory seemed a sure thing as the Indians looked ahead to what they thought would be their 3rd World Series appearance in five seasons. The Red Sox won game 3, and smoked the Indians 23-7 in a memorable game four before coming back to the Jake for game five. The game was tied 7-7 after three innings as both Saberhagen and Nagy got shelled, and in came Pedro Martinez…who had elected not to start the game due to a pulled muscle in his back. Pedro no-hit the Tribe for the final six innings, leading the Bosox to a 12-8 win.This is the only game on this list I have attended, and also led to the firing of Mike Hargrove … which happened on the same day as my first date with the woman I would end up marrying.