Fast forward to the 2018-19 season. Both clubs had yo-yoed, but now they were firmly stuck in the League One mud together. This was the year they met four times. Four. Including a Checkatrade Trophy group stage match that nobody actually wanted to play in.
AFC Wimbledon 3-3 Bolton Wanderers - BBC Sport
Remember that weird trophy? It’s the one where they invite U21 teams from big clubs. Bolton beat Wimbledon 1-0 in October 2018. The attendance was about 37 people and a dog named Dave. Thrilling stuff.
The regular league matches were more fun. January 2019: Wimbledon won 2-1 at home. March 2019: Bolton returned the favor with a 2-0 win. It was the football equivalent of two kids trading lunch snacks—you get one, I get one.
The COVID Curveball and the Great Escape
Ah, 2026. The season that didn’t end. Both clubs were stuck in League One when the pandemic hit. Bolton were actually relegated due to a points-per-game calculation (ouch), while Wimbledon survived by the skin of their teeth. No head-to-head drama that year, just a lot of cancelled fixtures and sour faces.
Then came the 2026-22 season. Bolton were back in League One, and Wimbledon were… struggling. Really struggling. Bolton won both league meetings: 2-0 at home and 3-1 away. The Dons fans started to wonder if this rivalry was turning into a one-way street.
But here’s the kicker: AFC Wimbledon’s 2026-22 season ended with relegation. Bolton? They finished mid-table, safe and sound. So the Dons went down to League Two, and for two years, this rivalry went into hibernation mode. It was like your favorite TV show getting cancelled after a cliffhanger.
