Michael Chandler’s third-round TKO loss to Paddy Pimblett at UFC 314 was both shocking and decisive. For a fighter once hailed as a title contender with a reputation for chaos and violence inside the Octagon, this latest defeat—his third straight and fifth in six UFC outings—puts his career at a pivotal crossroads. At 38 years old, Chandler remains one of the most entertaining fighters on the roster, but he may be nearing the end of his competitive window.

The long-discussed super fight with Conor McGregor still looms in the background, but with McGregor's extended layoff, legal troubles, and uncertain return timeline, banking on that bout happening might be wishful thinking. If McGregor ever returns, this remains the highest-reward, highest-profile fight Chandler could land. But if that fantasy match-up doesn’t materialize soon, retirement may be the most logical next step.

Chandler has accomplished more than most: a three-time Bellator lightweight champion, a multiple-time UFC post-fight bonus winner, and a fan-favorite for his never-back-down style. With diminishing returns in competition and no clear path to contendership, Chandler must ask himself if there’s anything left to prove—or if the legacy he’s built is enough.

If Conor McGregor returns to the UFC in 2025, a Chandler vs. McGregor showdown remains a blockbuster that makes sense for both athletes—two aging stars known for explosive fights, waning title relevance, and massive fan appeal. If McGregor stays inactive, the UFC should allow Chandler the dignity of a retirement fight, ideally on a major card where his contributions can be celebrated.

Chandler vs. McGregor is pure dynamite. Both fighters are aggressive strikers with one-shot knockout power. Chandler’s wrestling would pose a legitimate threat to McGregor’s historically suspect takedown defense, while McGregor’s precision and timing on the feet could expose Chandler’s tendency to charge in recklessly. It’s a fan-friendly clash of styles that’s both dangerous and winnable for either man, depending on their current forms.

If Chandler vs. McGregor happens, it's a pay-per-view co-main or even headliner—particularly if neither is chasing a title. A perfect fit would be International Fight Week or a year-end mega event. If not McGregor, a retirement fight for Chandler could slot nicely as a featured bout on a numbered card with veteran flair—perhaps UFC 320 or 321.

Last 5 Fights – Michael Chandler

* ❌ Loss vs. Paddy Pimblett — TKO (elbows and punches), UFC 314, April 12, 2025
* ❌ Loss vs. Charles Oliveira — Decision (unanimous), UFC 309, November 16, 2024
* ❌ Loss vs. Dustin Poirier — Submission (RNC), UFC 281, November 12, 2022
* ✅ Win vs. Tony Ferguson — KO (front kick), UFC 274, May 7, 2022
* ❌ Loss vs. Justin Gaethje — Decision (unanimous), UFC 268, November 6, 2021

Last 5 Fights – Conor McGregor

* ❌ Loss vs. Dustin Poirier — TKO (doctor stoppage), UFC 264, July 10, 2021
* ❌ Loss vs. Dustin Poirier — TKO (punches), UFC 257, January 24, 2021
* ✅ Win vs. Donald Cerrone — TKO (head kick and punches), UFC 246, January 18, 2020
* ❌ Loss vs. Khabib Nurmagomedov — Submission (neck crank), UFC 229, October 6, 2018
* ✅ Win vs. Eddie Alvarez — TKO (punches), UFC 205, November 12, 2016