I made a market with the exact same question but for May 2023 that resolved yes (as in, I did beat him). His plan was to tail me for the length of the race, but wasn't able to keep up as of 0.25 miles in; he subsequently gave up.

Since May 2023, I've ran a few shorter (10K or so) races, and a marathon this past month (with a time of 4:34). I'm currently training for another marathon in March; I'm doing some speedwork but definitely not doing specialized training for shorter distances. My goal MPW is around 45.

Since May 2023, he's been exercising a lot more and dropped 10+ (I think?) pounds. He's playing tennis consistently. He's eating healthier. Historically, he's a pretty fit/ athletic dude.

TBH, I think I'll beat him again but he wants me to try opening the market again. Good luck!