That day in particular remains with him, Maddon said, because it was a day he realized how special his team could be.
One can only guess that when Maddon envisioned his ideal future, it would most definitely contain games like Monday's 1-0, 11-inning walk-off over the Yankees. It was not only a hard-fought victory that featured two elite arms, but the Rays knocked the former American League East leaders from their perch atop the division.
"It was kind of a Frasier-Ali; it was all there," Maddon said. "Both guys were absolutely incredibly good tonight. They were."
It was a face off that had been built up for some time -- David Price for Tampa Bay; CC Sabathia for New York. Though Yankees faithful may have left Tropicana Field with a sour taste in their mouths over the final score, both parties got exactly what they came to see.
Tampa Bay's win not only put the club at 87-56 -- the best record in baseball -- but moved the Rays ahead of New York and into first place in the AL East by a half-game. The last time the Rays were in sole possession of first place was Aug. 3. It was also the first time in the history of the franchise the Rays had won 1-0 on a walk-off, and it was also the team's first extra-inning win with that score.
"We've got to bounce back," said New York manager Joe Girardi, whose team has lost seven of its last eight games. "We've had three tough losses on this road trip, really tough losses, but this is a team with a lot of character and we'll bounce back."
The idea of a no-hitter on either side was banished by the bottom of the third inning, when Rays catcher Kelly Shoppach lined a single to right to break up Sabathia's bid. Price lost his shot when Yankees shortstop Derek Jeter singled to right on the second pitch of the first inning. Still, there was nothing about the ensuing battle that betrayed any bit of the hype surrounding it. Each lefty tossed eight innings of scoreless ball, which left things up to the bullpens in the ninth.
And the 10th. And the 11th.
Rafael Soriano slammed the door on New York with little trouble, as did Joaquin Benoit and Grant Balfour behind him. Meanwhile, the Rays steadily picked at New York's bullpen until they found a weak link: Sergio Mitre, the fifth Yankees pitcher to take the mound.
The result came in as dramatic a fashion as was staged by the entire game, with Reid Brignac sending a Mitre offering screaming into the right-field stands on a full-count pitch in the bottom of the 11th for the game-winner.
"[It was] unbelieveable. You just feel like you're floating on clouds," said Brignac, who had seen action in just five games since rosters expanded Sept. 1. "I had a couple of walk-offs in the Minor Leagues, but nothing compared to this."
It all was a fairytale ending that nearly didn't get written: Brignac entered the game in the top of the 10th inning as a replacement for left fielder Carl Crawford, who was ejected for arguing balls and strikes one inning prior.
"That [last] one probably was a strike. It was still close, but throughout the game I was just getting frustrated, and that was just it, I just kind of exploded," Crawford said. "[Reid] definitely came through for us. ... He hit the home run and won it for us. I don't think I would've done that tonight, I was struggling at the plate a little bit tonight, so I'm just glad for Reid."
Maddon had more reason to smile than just the win: Earlier in the day, he had spent some time reflecting on a doubleheader at Yankee Stadium early in his managing career, one with a not-as-favorable conclusion.
"We just got lambasted for two games," Maddon remembered. "[New York] scored near 20 points in each of the two games, and I'm standing on the top rail and I'm just imagining the better days and knowing that they were going to come. When you finally break through, and you're able to come out on the other side and know that you can play with these guys, obviously it's night and day. It's black and white. It's all of those polar opposites.
"It's a great feeling to know that we've come to this point, to know that we can compete with the most dominant franchise of the century, one of the best in all sports over any period of time -- it's good to know that."
If there was any doubt the Rays would compete with the Yankees this season, it was erased Monday night, when just three hitters reach second base during the first eight innings. After Jeter's first-inning single, Price locked in to retire the next 14 consecutive Yankees. The 15th, catcher Jorge Posada, drew a two-out walk in the fifth, but was thrown out trying to steal second base a moment later to end the inning.
Price had pregame praise lavished upon him by Maddon, who said his young lefty was cool, calm and nearly unflappable. The 25-year-old not only made good on every last compliment he received, but went a step further in permitting the powerful Yankees lineup a single hit through his first 6 1/3 innings of work.
"[Sabathia] is good, but David is definitely approaching that category of pitching esteem," Maddon said. "For those who are still on the fence in regards to a Cy Young vote, I'm sure they're still on the fence."
Though he walked two, for every batter on, Price fought back until his defense retired the side. When he exited in favor of Soriano after the eighth, he did so to a standing ovation.
Sabathia earned his cheers, too. The burly lefty didn't even sniff trouble until the eighth inning -- when Sean Rodriguez led off with a single -- punching out nine and walking two along the way.
When the end came though, it came swiftly. Pinch-hitter Dioner Navarro bunted up the first-base line to move Rodriguez to second, and Sabathia plunked the next hitter, Shoppach, to put two on with one out. Sabathia caught B.J. Upton swinging on a third strike for out number two and got Jason Bartlett to ground out to end the inning, but that was all Tampa Bay would have to see of the 6-foot-7 southpaw.
From there, the Rays lay patiently waiting for the right time to attack. Eventually, they would find it in Brignac.
"We just haven't got the bounces, haven't gotten the breaks," Sabathia said.
Dawn Klemish is a contributor to MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.