That loss dropped the Padres to 48-81, certainly a far cry from where they are now, just two seasons later.
The Padres, coming off a 7-3 road trip to San Francisco, Chicago and Milwaukee, open their a three-game series with Arizona on Tuesday at PETCO Park with a 74-59 record and a six-game lead over the Giants in the National League West.
The turnaround, to be sure, has been nothing short of stunning; especially given a payroll running shy of $40 million. Stunning maybe, but as fourth-year manager Bud Black is quick to caution, it isn't miraculous.
Yes, Black said to a team in the doldrums, stuck in the cellar, this can happen to you, too.
"I think what that tells me is that you can suffer through a bad year and things can turn around -- and that things can get better," Black said. "It doesn't mean that because you're not playing well that you have to continue like that.
"We realized that we did have to make some changes on the roster. A lot of times, you can't completely overhaul a roster overnight."
So how did the Padres get from that 99-loss season to where they are today? First of all, they upgraded the roster -- starting with former general manager Kevin Towers and now first-year general manager Jed Hoyer. The moves are too numerous to name.
But getting from there to here, those who are still around will agree, wasn't very fun.
The 2008 roster, one assembled by Towers, included Jim Edmonds -- who was released in May. Veteran Tony Clark struggled and was traded back to Arizona in July. Jake Peavy and Chris Young spent time on the disabled list -- and Randy Wolf and Greg Maddux were eventually jettisoned for greener pastures.
In May of that season, Towers, having seen enough of what he considered to be subpar play, sounded off to the media.
"We're bad, no question about it," Towers said at the time. "You can't just say it's early in the season. I haven't seen any signs in the last couple weeks that lead me to believe -- or our fans to believe -- we're going to turn this thing around.
"It's up to the guys in this clubhouse. I am certainly not going to watch this for four more months. You're looking for even a little bit of progress. It's like Groundhog's Day, over and over."
Those 2008 Padres included Rule 5 infielder Callix Crabbe, outfielder Chip Ambres and second baseman Tadahito Iguchi -- who was released in September. There were plenty of more players used along the way, players who were never seen or heard from again.
The Padres' Opening Day lineup in 2008 itself included outfielders Brian Giles and Paul McAnulty, shortstop Khalil Greene and catcher Josh Bard.
"It was really tough. No matter the team you have, you want to win," Black said. "We're all competitive, we all have pride. What was frustrating was we knew we didn't have the complete 25-man roster that we needed to make strides forward.
"If you get the right players, you can upgrade your team."
Look at what Hoyer accomplished in the offseason -- signing free agents like infielder Jerry Hairston, pitcher Jon Garland and catcher Yorvit Torrealba. He also traded for outfielder Scott Hairston.
In terms of roster turnover, the 2008 Padres used 32 different pitchers in those 99 losses -- including 14 starting pitchers. The 2010 Padres have used 17 pitchers and seven starters, and two of those -- Tim Stauffer and Chris Young -- made only one start apiece.
These Padres have just one three-game losing streak. In fact, no other team in the Major Leagues can boast of having one solitary three-game losing streak this season.
"Where it helps us is that when things are going bad now, if we lose two games in a row -- if you call that bad, you know there's a light at the end of the tunnel," Padres closer Heath Bell said. "We all believe that if [we] keep working hard, the winning will take care of itself."
In 2008, the Padres lost at least three consecutive games 13 times -- including losing skids of six, seven and eight consecutive games.
"I think when you're going through it, it's not that fun at all," said Padres third baseman Chase Headley, who was trying to prove himself at the Major League level in 2008.
"You're going through long stretches where it feels like the season is 300 games long. Having gone through that, though, it makes you appreciate this now."