John Calipari’s Kentucky Wildcats will enter this NCAA Tournament as a 2 seed — a designation that has brought both happiness and heartbreak to UK fans over the years.

Since the tournament expanded to 64 teams in 1985, the Cats have earned a 2 seed on five occasions. Here’s a look at how Kentucky has fared in those seasons:

1988

Ranked No. 1 nationally at one point in the season, Eddie Sutton’s Wildcats won the SEC Tournament and defeated Southern and Maryland in the NCAA Tournament’s opening weekend in Cincinnati to advance to the Sweet 16 and a date with 6-seeded Villanova. Super sophomore Rex Chapman scored 30 points and dished out five assists against those Wildcats, but it wasn’t enough to prevent an 80-74 Villanova victory.

That was the final game for Chapman — who was selected with the No. 8 pick in that year’s NBA Draft — as well as seniors Ed Davender, Winston Bennett, Rob Lock, Cedric Jenkins and Richard Madison. The tournament appearance was later vacated by the NCAA following the investigation into Sutton’s program, and Rick Pitino was hired as the Wildcats’ coach a year later.

1992

The Cats made their first NCAA Tournament appearance in four years following the end of the Sutton era and the two seasons of probation that followed.

The Unforgettables and sophomore star Jamal Mashburn led UK to an SEC Tournament title followed by victories over Old Dominion, Iowa State and Massachusetts — the Minutemen coached by 33-year-old John Calipari and featuring junior forward Tony Barbee.

With a trip to the Final Four on the line, Pitino’s Wildcats met defending national champion and No. 1-ranked Duke, led by Christian Laettner, Bobby Hurley and Grant Hill. In one of the greatest games ever played — and the final game of UK broadcaster Cawood Ledford’s legendary career — Sean Woods put the Cats ahead with an unbelievable runner over Laettner with 2.1 seconds left. You know what happened next.

1998

Kentucky fans should hope for a repeat of this one.

In Coach Tubby Smith’s first season, the Wildcats lost just four times — though three were at Rupp Arena, and one was to Louisville — and entered the NCAA Tournament with the No. 5 national ranking.

A team without stars — Jeff Sheppard was the leading scorer at 13.7 points per game — but plenty of depth romped to double-digit victories over South Carolina State, Saint Louis and UCLA before meeting top-seeded Duke in the Elite Eight. The “Comeback Cats” fell behind by as many as 18 points in a nightmare of a first half, and they trailed by 17 with less than 10 minutes left in the game. Somehow, UK managed a victory, aided by late three-pointers from Cameron Mills and Scott Padgett that will live on forever in Wildcats lore.

Kentucky defeated Stanford (in overtime) in the national semifinals, and the Cats had one more comeback in them — erasing a 10-point halftime deficit to beat Utah in the title game and claim the program’s seventh national championship. That UK team is one of only five 2 seeds to win the NCAA Tournament since the field expanded in 1985. The others are Louisville in 1986, Duke in 1991, UConn in 2004 and last year’s Villanova Wildcats.

2001

UK started the season with back-to-back losses — to St. John’s and UCLA — and an early defeat to Penn State in Rupp Arena, where Joe and Jon Crispin combined to make 13 three-pointers and score 57 points in a major upset.

Led by junior Tayshaun Prince and sophomore Keith Bogans, the Cats rebounded to win the SEC regular-season and tournament titles and earn a 2 seed in the NCAA Tournament, where Tubby’s group nearly lost to 15-seeded Holy Cross on the first day. (Kentucky won 72-68 in a game that was tied with 6 minutes left).

UK then beat Iowa in the round of 32 before a wild Sweet 16 game against 6-seeded Southern Cal, which blew the doors off the Cats early — leading 31-10 at one point — before a couple of furious Kentucky comebacks to get within one point with under a minute left. The Trojans finished the job for an 80-76 victory.

Prince, who scored a total of 58 points in UK’s first two tournament games, had just six points against USC. It capped a bad week for Kentucky fans: Rick Pitino had been hired as Louisville’s coach two days earlier.

2005

In Tubby Smith’s final good season at UK — by local standards — the Cats appeared to be well on their way to a 1 seed, taking a 23-3 record and No. 3 national ranking to Florida for the regular-season finale. The unranked Gators beat UK in Gainesville and did it again in the SEC Tournament title game — the latter win a 70-53 rout.

So the Cats settled for a 2 seed, defeated Coach Travis Ford and Eastern Kentucky in the first round, beat Cincinnati in a wildly entertaining round of 32 game — and Coach Bob Huggins’ last with the Bearcats — and then took care of national player of the year Andrew Bogut and Utah in the Sweet 16. That set up a matchup with 5-seeded Michigan State, a trip to UK’s first Final Four in seven years on the line.

With UK down by three points in the final seconds, a hectic final possession ended with the ball in Patrick Sparks’ hands at the top of the key, and the Wildcats guard let fly a double-clutch attempt at the buzzer. The ball danced around on the rim and finally fell, and the officials spent more than 5 minutes reviewing the shot, ultimately ruling that Sparks’ feet were behind the three-point line. The three was good, the game was tied, but the Cats would fall, 94-88, after two overtimes.

“It will go down in history as a great college basketball game,” Smith said. “It hurts right now, but some of our guys will appreciate it later on.” Smith left UK for Minnesota two years later.