- May 5 127th Kentucky Derby: Jorge Chavez aboard Monarchos wins in 1:59.97
- May 9 Accra Sports Stadium Disaster: 129 Ghanaian football fans die in a stampede caused by the firing of teargas by police following a decision by the referee in a crucial match between arch-rivals Accra Hearts of Oak and Kumasi Asante Kotoko
- May 12 English FA Cup Final, Millennium Stadium, Cardiff (72,500): Liverpool beats Arsenal, 2-1 with Michael Owen scoring twice for the Reds
- May 18 101-year-old Harold Stilson becomes oldest golfer to record a hole-in-one when he aces the 108-yard, par-3, 16th hole at Deerfield CC, FL
- May 19 126th Preakness: Gary Stevens aboard Point Given wins in 1:55.40
- May 19 Manchester United lose 3-1 to Tottenham at White Hart Lane but win English Premier League title for the 3rd consecutive season
- May 21 NHL Western Conference Final: Colorado Avalanche beat St. Louis Blues, 4 games to 1
Laureus Awards
May 22 Laureus World Sports Awards, Grimaldi Forum, Monaco: Sportsman: Tiger Woods; Sportswoman: Cathy Freeman; Team: French Men's National Football team
- May 22 NHL Eastern Conference Final: New Jersey Devils beat Pittsburgh Penguins, 4 games to 1
- May 23 9th UEFA Champions League Final: Bayern Munich beats Valencia (1-1, 5-4 on penalties) at Milan
- May 23 Marco Siffredi becomes the first person to snowboard down Mount Everest via the Norton Couloir (some share record accreditation with Stefan Gatt)
- May 26 Super Rugby Final, Canberra: Fullback Andrew Walker kicks 5 penalties & 3 conversions as the ACT Brumbies win their first title; beat Coastal Sharks (Durban), 36-6
- May 27 Indianapolis 500: race rookie Hélio Castroneves of Brazil leads for the final 52 laps to win first of 4 Indy 500s; Penske Racing sweeps 1st-2nd with Gil de Ferran the runner-up
Senior PGA Championship
May 27 Senior PGA Championship, Ridgewood CC, NJ: 5-time British Open champion Tom Watson wins first of 6 Champions Tour major titles with a 1 stroke win over Jim Thorpe
- May 29 U.S. Supreme Court rules that disabled golfer Casey Martin can use a cart to ride in tournaments
Baseball Players
Basketball Stars
Boxers
Footballers
NFL Stars
Tennis Champions