Given their franchise’s rich basketball history, the Milwaukee Bucks have their fair share of heated rivalries over the years.

While the all-time Bucks roster has been blessed to employ some of the biggest names in the sport, several opposing players also managed to give them fits in numerous playoff battles.

The Chicago Bulls, Boston Celtics, Los Angeles Lakers, Philadelphia Sixers, and the Toronto Raptors are just some of the teams that antagonized the Bucks over the years. Today, we will list down the five opposing players that Milwaukee had the most trouble with.

Kawhi Leonard

This seems a bit of a stretch considering Kawhi Leonard’s tenure with the Raptors lasted for just one season. However, the case could be made that current Bucks superstar Giannis Antetokounmpo could have championship experience by now had Leonard not spoiled his plans.

Antetokounmpo, who eventually received his first MVP award by the 2018-19 season’s end, was widely viewed as the best player on the floor in the 2019 Eastern Conference Finals. But Leonard, who already has one title under his belt at the time, proved pundits otherwise.

Pundits across several Bucks news outlets expected Milwaukee to cruise to a Finals trip after winning the first two games of the best-of-seven affair. But once the series shifted back to Toronto, Leonard completely turned things around. He roasted the Bucks with averages of 29.8 points, 9.5 rebounds, 4.3 assists, and 2.2 steals in six intense games.

The Klaw dropped those amazing numbers all the while defending Giannis on the other end. Toronto swept the next four games against Milwaukee and eventually won the title against the Golden State Warriors in the Finals.

Larry Bird

The Bucks boasted an intimidating line-up in the ‘80s led by Bob Lanier, Sidney Moncrief, and Terry Cummings, among others. During that stretch, the team valiantly tried to repeat recapture the title they last won in 1971.

The team constantly reached the playoffs during that decade but failed to emerge out of the East mainly due to the utter dominance of the Boston Celtics. While the C’s bruising bigs Kevin McHale and Robert Parish gave them troubles, it was the all-around brilliance of Larry Bird that dashed their title hopes.

Bird’s genius was evident in the 1986 ECF, where he torched Milwaukee with his scoring and passing. The Celtics swept the Bucks in four games, with Bird delivering the killing blow in the final game, where he dropped 30 markers.

Julius Erving

While Bird was the Bucks’ biggest tormentor in the ‘80s, Dr. J was a close second. Milwaukee faced Philly six times in seven years from 1981-87. Unlike Boston who completely had their number, the Bucks managed to hold their own against the Sixers during that time.

Still, the Sixers were considered the more successful team out of the two. Julius Erving singlehandedly willed the 76ers to victory in Game 7 of the East semis against the Bucks in 1981.

The two teams figured in another Game 7 in the 1986 semis. Dr. J slowed down a bit back then, but he still had Bobby Jones and a young Charles Barkley to back him up. However, the Bucks exacted their revenge and won the do-or-die match.

Allen Iverson

The Sixers-Bucks rivalry continued into the early 2000s at the time when Milwaukee was bannered by Ray Allen. The team complemented Allen’s scoring with gritty players like Glenn Robinson, Sam Cassell, and Tim Thomas.

However, a 6-foot guard completely stifled their chances of reaching the Finals back in 2001. Allen Iverson was the bane to the Bucks defense, as they had no answer (pun intended) to his scoring exploits.

Allen and AI went at it in the ECF, as the series went the distance for a pivotal Game 7. Iverson, whose 46 points went for naught in Game 6, followed up with a 44-point explosion in Game 7. This time, the Sixers team completed the job and secured a trip against the Lakers in the Finals.

Kareem Abdul-Jabbar

Milwaukee does have a love-hate relationship with one of the best players of all time. After all, Kareem Abdul-Jabbar — who was still Lew Alcindor back then — led the Bucks to its first and only title in 1971.

However, Kareem’s public wish to be traded to a big market team in 1974 left a bad taste to a lot of Bucks fans back then. Abdul-Jabbar’s success has been so synonymous with the Lakers that not a lot of people remember his tenure in Wisconsin. Adding insult to injury was the fact that the Lakers were one of the Bucks’ biggest rivals at the time.

Milwaukee played in the Western Conference back then and often clashed with the Lakers in the postseason.