Both men were long-serving stalwarts in north London prior to taking on new challenges.
Oxlade-Chamberlain was the first to head for the exits, as he swapped Emirates Stadium for Anfield in the summer of 2017, with the versatile midfielder having struggled to hold down a regular role under Arsene Wenger.
With his contract also running down, the 24-year-old jumped at the chance to link up with Liverpool.
"It's an amazing place to play, it was stable, you build relationships, but I felt I had to do it for football reasons to try and better myself.
"I've loved every minute so far. It was always horrible coming here [Anfield] as an opposition player but the crowd gives you goosebumps. To hear them singing for you is unbelievable."
A few months after seeing Oxlade-Chamberlain head for Merseyside, Walcott did likewise during the winter transfer window.
A £20m deal took him to Goodison Park, with the 29-year-old also aware of the need to find regular football after slipping down the pecking order at Arsenal.
He said on the reasons for his switch after 12 years with the Gunners: "I feel it was the right time. The loyalty I had for Arsenal and Arsene Wenger meant I could do it the right way.
"It was time for me to experience something different but still be competitive.
"The season didn't start off how we wanted but Everton are going in right direction.
"I never knew what it was going to be like having been at Arsenal for so long and coming to somewhere completely different, but the fans have taken to me and been so welcoming.
"I'm pleased with how passionate they are, it's one reason why I came here because I feel like they're competitive and want to improve. The first time walking about at Goodison Park... you can't explain it.
"Then, when I scored my first goal, the emotion came out. It was about enjoying my football again."
Oxlade-Chamberlain and Walcott will be reunited this weekend when Liverpool make the short trip across Stanley Park to take on Everton in the 231st Merseyside derby.