here’s a weird one: petr sykora
over a 17 year career that began as a teenager, he played in six finals. twice his team won, but he was injured when the final whistle blew. but he was on the ice for all four losses.
2000: his team won the cup but he was at the hospital after derian hatcher smoked him in the first period cutting across the middle
2001: devils lost to colorado in game seven
2003: ducks lost to his old team, the devils, in game seven
2008: penguins lost to detroit in game six
2009: penguins won the rematch but sykora, nearing the end of his (first) NHL tenure, was no longer an everyday player by the playoffs. after getting scratched in the second round to make room for miro satan’s return, sykora didn’t get back into the lineup until game six of the finals, where he broke his leg blocking a shot. pens won in game seven, with satan regaining his spot in the lineup.
2012: after a year in europe, a rejuvenated sykora returns to the devils and plays all 82 games (20 goals alongside an also rejuvenated elias, who bounced back to finish top ten in scoring) and continues being an everyday player in the playoffs. he was taken off elias’ line in the playoffs so he didn’t make much noise during their finals run, but he did score this goal, showing he still had some wheels and scoring touch left:
in the third round, down 2-1 to the rangers, he was replaced in the lineup by 20 year old recent first rounder jacob josefson, but got his spot back in game three of the finals with new jersey staring down a 3-0 deficit. with sykora back, they won two to claw back into the series (though sykora didn’t personally contribute much on the scoreboard) before losing the cup in game six with sykora on the ice.
in the end, this was the closest he got to skating around the ice with the cup: