Crawford went 2-for-3 with a triple and a run scored in an instructional league game on Tuesday morning at Tropicana Field and was 0-for-4 and hit by a pitch on Monday.
"For me Monday and Tuesday were a success," said Rays executive vice president of baseball operations Andrew Friedman, who watched Crawford's performance with Maddon on Tuesday morning.
"A week ago it was very clear he wasn't ready. Ten to 14 days from now it will be very clear that he is ready. So we are in this gray area [of his recovery] right now."
Although Friedman said prior to Tuesday's team workout that getting Crawford another tuneup day would give him a little more "peace of mind," the Rays announced later on Tuesday afternoon that Crawford would not play in the instructional league on Wednesday.
The change in plans is more of a positive reaffirmation, as Maddon admitted the team hadn't talked about Wednesday's workout specifically and the skipper also wanted to get Crawford's opinion.
The 27-year-old Crawford was activated prior to Friday night's game against the Tigers, and had been on the disabled list since Aug. 10, recuperating from surgery performed on Aug. 14 to repair the subluxation of his right middle finger tendon.
Crawford came through his initial workout on Monday with no reported pain, and was hopeful that he could convince the Rays that he was healthy enough to play in the first round of the playoffs.
"I don't have an explanation why it got better," Crawford said of his ahead-of-schedule recovery. "It just did."
Regardless of the reasons why, Crawford's return is a pleasant surprise for Maddon and the Rays.
The outfielder was hitting .273 with eight home runs, 10 triples and 57 RBIs at the time of his injury. He also had 25 stolen bases and will be a huge upgrade with his speed and defense in left field.
Although Maddon expected to bat Crawford farther down than his traditional No. 2 hole, the Rays manager still believes the two-time AL All-Star will provide a "tremendous" boost.
"I was telling the other guys you send a lineup card over to the other side and it has his name on it, there's a lot more angst created as [opposed] to when it's not," Maddon said. "From our perspective there's a big [level of] confidence."
Crawford's extended absence away from Tropicana Field has helped him nurse his hamstrings back to 100 percent. The artificial turf in the Rays' home dome has caused nagging soreness in both of Crawford's hamstrings this season, but the outfielder said Monday that his rested legs were fresh and ready for the field.