And as is the case with Lee, Westbrook's outing left him with more questions than answers.
"I can't put my finger on it," Westbrook said. "I've felt good, but things haven't been going my way."
When Westbrook's on the mound, things haven't been going the Indians' way, either. He hasn't posted a victory over his last seven starts, dating back to April 27. That's his longest stretch without a win in his career.
Not long after watching Westbrook surrender four first-inning runs to the Red Sox, manager Eric Wedge was asked if he's concerned about the right-handed sinkerballer.
"I believe in Jake," Wedge said. "He's going to come around. I feel strong, in terms of my confidence in him. He does too many things right not to work through this."
But in trying to bounce back from Westbrook's early troubles in this one, the Indians did little right in their approach against left-hander Jon Lester.
Lester was the feel-good story in what was a feel-bad night for the Tribe. He was making his first big-league appearance since being diagnosed with treatable lymphoma last August and enduring six rounds of chemotherapy.
Now cancer-free, the 23-year-old Lester didn't look any worse for the wear, tear and wait. And Westbrook gave him quite a comfortable cushion to work with.
In the first inning, Westbrook let the first three batters he faced aboard. Manny Ramirez then lined a two-run double to left, and J.D. Drew followed with a bloop RBI single to right.
Westbrook finally got his first outs of the inning when Mike Lowell hit into a double play, but another run came across in the process. It was already 4-0, Red Sox.
So what happened? Well, the response from Westbrook wasn't overly analytical.
"I gave up a lot of runs," Westbrook said. "A lot of hits and a lot of runs. I wasn't very good in the first inning. I made some bad pitches, and they capitalized on them."
His day didn't get much better in the second. Coco Crisp, making his first appearance at The Jake since the January 2006 trade that sent him to Boston, led the inning off with a double and later scored on Kevin Youkilis' single to make it 5-0.
But Lester didn't need all that support. Especially not against an Indians' offense that took some bad hacks at pitchers' pitches.
In six innings against Lester, all the Indians managed was Grady Sizemore's two-run homer to right in the third.
They squandered their best chance to get into the ballgame in the fourth, after loading the bases with one out. Josh Barfield hit a weak grounder back to the mound, which Lester sloppily fielded and threw home for the forceout. Sizemore then went down swinging to end the threat.
"We helped him out a little bit chasing some high fastballs," Wedge said of the approach to Lester. "But the guy showed some poise out there. His rhythm was in control. He went out there and pitched. I think he recognized we were helping out a little bit and kept doing it. We had opportunities there, but that one inning, in particular, we weren't able to take advantage of."
Wedge declined to offer up the Indians' travel woes as an excuse for the offensive funk. The team charter from Texas didn't touch down in Cleveland until close to 5 a.m. ET Monday.
"That's just part of the big-league season," Wedge said.
If this game had a bright spot, where the Indians were concerned, it was in Westbrook's ability to bounce back from that early rough patch and save the bullpen from getting worn down. He lasted six innings, holding Boston scoreless on four hits in the third through sixth.
"He had that feel back," Wedge said, "and he looked like that guy we need to start the game out."
Lee had that look in the innings that followed the five-spot he let the Rangers put up against him in the first inning of Saturday's ballgame.
The Indians are just waiting for Westbrook and Lee to find that form a little earlier and a little more often in their starts.
"I think they're both closer," Wedge said. "I don't want to compare one to the other. They are two different situations. But they're both closer. Hopefully they're both ready to take off for us."