No league has it worse than basketball tbh
Finals winners, 2017 to 1999:
Warriors
Cavs
Warriors
Spurs
Heat
Heat
Mavericks
Lakers
Lakers
Celtics
Spurs
Heat
Spurs
Pistons
Spurs
Lakers
Lakers
Lakers
Spurs
If you want to go beyond winners
NBA Finals appearances, 1999-2017:
Spurs 6
Lakers 7
Mavericks 2
Warriors 3
Thunder 1
Knicks 1
Pacers 1
76ers 1
Magic 1
Nets 2
Pistons 2
Heat 5
Celtics 2
Cavs 4
14 teams. The last 3 Finals being the same matchup
Super Bowl appearances, 1999-2017:
Broncos 3
Falcons 2
Rams 2
Titans 1
Ravens 2
Giants 3
Patriots 7
Buccaneers 1
Raiders 1
Panthers 2
Eagles 1
Steelers 3
Seahawks 3
Colts 2
Bears 1
Cardinals 1
Saints 1
Packers 1
49ers 1
19 teams. One repeat SB matchup in that same timespan, 4 years apart