The Wizards dumped not one but two coaches in setting the MLS record for worst opening to a season.
Flash forward 13 years. Toronto is 0-6-0 and Winter still has a job heading into Saturday's game at Real Salt Lake's fortress at Rio Tinto Stadium.
He may be looking over his shoulder if history says anything.
But there also could also be light at the end of the TFC tunnel, judging from the Kansas City experience more than a decade ago.
The Wizards pulled the trigger on manager Ron Newman after four losses in '99. Assistant coach Ken Fogarty took over as interim coach for three more defeats, then was let go when former U.S. national team boss Bob Gansler took over.
In those days, Kansas City didn't even have the luxury of a tie. The MLS resorted to shootouts to ensure a winner.
Alexi Lalas, a defender for the Wizards that year, recalls how the losing streak snowballed.
"Most players go through a bad streak at some point in their careers. It's never fun and at the time it was excruciating for all involved, but the memory has softened with the years," Lalas said in an email to The Canadian Press.
"We had a great collection of players that just didn't click. The best-laid plans. Then you start to flounder and then it seems the harder you fight, the harder it is to be saved. You can lose faith in yourself, your teammates and your coach."
Ironically, the '99 Wizards team featured two players who would go on to coach Toronto FC: Mo Johnston and Preki (the two were fired together in September 2010 when Johnston was the team's director of soccer and Preki his coach). Adding to the connection is the fact that Gansler spent 2007 as an assistant coach for Toronto FC.
Rob Thomson, who today is Sporting Kansas City's vice-president of communications, was head of public relations for the Wizards in '99.
He remembers a team ravaged by injuries in goal to Tony Meola and Chris Snitko and with few attacking options early that season.
The goalkeeper gloves initially went to Mexican Cesar Delgado and Thomson remembers having a bad feeling in the season-opening warmup when Wizards players were beating him on almost every shot.
They lost the opener 4-0 away to the Dallas Burn.
Delgado was slated to return home to Mexico after the game but instead returned to Kansas City with the team. His reward as he waited to leave for his flight later that evening was having to watch tape of the game while the rest of the team trained.
"Pretty cruel," said Thomson.
The losses mounted: 3-0 to Chicago, 1-0 to New England, shootouts losses to San Jose and in Colorado after 1-1 ties, 1-0 in Miami and 1-0 to Columbus.
Kansas City scored just twice during the losing streak.
"The worst thing about it I remember was we had long road trips everywhere," Thomson said of that season. "We were travelling to the East Coast and West Coast ... Going on these long trips was very, very tough."
Lalas recalls that spirits didn't change that much when Kansas City finally snapped the losing streak in Gansler's first game — a 2-1 win over Los Angeles Galaxy 2-1 at Arrowhead Stadium.
"Ultimately K.C. changed the coach which helped a little in the short-term, but the damage had been done. Even when we finally won a game there was still the feeling that it was just the odds catching up as opposed to any real breakthrough that was going to fundamentally change our fortunes," said Lalas, who scored in the win.
But Thomson says the arrival of Gansler was a huge turning point.
"When Coach Gansler took over, everyone's mindset totally changed."
Lalas and Thomson both offered words of encouragement to Toronto.
"Good news is that MLS has a short memory. The following year with some additions and subtractions (including myself), plus a healthy team, K.C. went and won the MLS Cup," said Lalas, now a TV analyst.
Added Thomson: "Hope springs eternal. Because the following year we started off the season 10-0-2 en route to the Supporters' Shield (by goal difference over Chicago) and then the MLS Cup.
"Some stuff that the team learned in '99 proved invaluable, of what we needed to fix."
The Wizards finished the 1999 season at 8-24 — thanks to a bookend seven-game losing streak at the end of the campaign — and set another MLS record in losing 16 straight on the road.
Amazingly the Wizards did not finish last, ending up five points ahead of the 7-25 New York/New Jersey MetroStars. Kansas City walloped the MetroStars 6-0 when they met in June.
Things turned for both teams in 2000, when the league switched to a three-conference setup.
The team bolstered its offence with Miklos (Danish Dynamite) Molnar, who became Canadian international Alex Bunbury's strike partner. Bunbury, whose son Teal now plays for Sporting Kansas City, had come on board midway through the '99 season.
Chris Klein and Chris Henderson were threats in midfield. Meola returned from injury and was named MLS Most Valuable Player, Goalkeeper of the Year and Comeback Player of the Year, conceding just 29 goals.
The Wizards finished the 2000 season at 16-7-9, three points ahead of the 17-12-3 MetroStars, and defeated Chicago 1-0 in the MLS Cup before 39,159 at RFK Stadium in Washington, D.C.
Kansas City set a record for most shutouts in a season (17), including a stretch of eight straight at home that saw them go 817 minutes without conceding a goal.
As Toronto FC looks down into the record book abyss, it can only wish the future looks so bright.