| Event | Venue | Date/Time | |
| Orlando City B vs. New York City FC II | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Sunday
8/3/2025
7:00 PM | view
tickets |
|
| Combat Night Pro Kissimmee | Events Center At Osceola Heritage Park
Kissimmee, FL | Saturday
8/9/2025
4:15 PM | view
tickets |
|
| Orlando City B vs. Chattanooga FC | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Saturday
8/9/2025
7:00 PM | view
tickets |
|
| Magik and Mythk Festival | Events Center At Osceola Heritage Park
Kissimmee, FL | Saturday
8/16/2025
11:00 AM | view
tickets |
|
| Orlando City B vs. Atlanta United II | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Saturday
8/23/2025
7:00 PM | view
tickets |
|
| Orlando City B vs. Crown Legacy FC | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Sunday
8/31/2025
7:00 PM | view
tickets |
|
| PPA Challenger Series Florida - Friday | Orange Lake Resort
Kissimmee, FL | Friday
9/5/2025
TBD | view
tickets |
|
| PPA Challenger Series Florida - Saturday | Orange Lake Resort
Kissimmee, FL | Saturday
9/6/2025
TBD | view
tickets |
|
| PPA Challenger Series Florida - Sunday | Orange Lake Resort
Kissimmee, FL | Sunday
9/7/2025
TBD | view
tickets |
|
| Orlando Tattoo Show | Events Center At Osceola Heritage Park
Kissimmee, FL | Friday
9/12/2025
TBD | view
tickets |
|
| Orlando Tattoo Show | Events Center At Osceola Heritage Park
Kissimmee, FL | Saturday
9/13/2025
TBD | view
tickets |
|
| Orlando Tattoo Show | Events Center At Osceola Heritage Park
Kissimmee, FL | Sunday
9/14/2025
TBD | view
tickets |
|
| Orlando City B vs. Huntsville City FC | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Sunday
9/21/2025
7:00 PM | view
tickets |
|
| Boots, Bulls & Barrels | Silver Spurs Arena
Kissimmee, FL | Saturday
10/4/2025
7:30 PM | view
tickets |
|
| Orlando City B vs. FC Cincinnati II | Osceola County Stadium At Osceola Heritage Park
Kissimmee, FL | Sunday
10/5/2025
1:00 PM | view
tickets |
|
| Ultimate Cards & Gaming Convention - 3 Day Pass | Events Center At Osceola Heritage Park
Kissimmee, FL | Friday
10/10/2025
TBD | view
tickets |
|
| Ultimate Cards & Gaming Convention - Friday | Events Center At Osceola Heritage Park
Kissimmee, FL | Friday
10/10/2025
12:00 PM | view
tickets |
|
| Ultimate Cards & Gaming Convention - Saturday | Events Center At Osceola Heritage Park
Kissimmee, FL | Saturday
10/11/2025
10:00 AM | view
tickets |
|
| Freestyle 40th Anniversary: George LaMond, Trinere, Shannon & Corina | Silver Spurs Arena
Kissimmee, FL | Saturday
10/11/2025
8:00 PM | view
tickets |
|
| Ultimate Cards & Gaming Convention - Sunday | Events Center At Osceola Heritage Park
Kissimmee, FL | Sunday
10/12/2025
10:00 AM | view
tickets |
|
| George Harris | Silver Spurs Arena
Kissimmee, FL | Sunday
11/9/2025
7:00 PM | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 1 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Monday
11/24/2025
1:00 PM | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 2 (Time: TBD) | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Monday
11/24/2025
7:00 PM | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 3 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Tuesday
11/25/2025
TBD | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 4 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Tuesday
11/25/2025
TBD | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 5 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Wednesday
11/26/2025
TBD | view
tickets |
|
| ESPN Events Invitational Adventure Bracket - Session 6 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Wednesday
11/26/2025
TBD | view
tickets |
|
| ESPN Events Invitational Imagination Bracket - Session 1 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Thursday
11/27/2025
TBD | view
tickets |
|
| ESPN Events Invitational Magic Bracket - Session 1 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Thursday
11/27/2025
TBD | view
tickets |
|
| ESPN Events Invitational Magic Bracket - Session 2 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Friday
11/28/2025
TBD | view
tickets |
|
| ESPN Events Invitational Imagination Bracket - Session 2 | State Farm Field House at ESPN Wide World Of Sports Complex
Kissimmee, FL | Friday
11/28/2025
TBD | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Tuesday
1/6/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Wednesday
1/7/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Thursday
1/8/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Friday
1/9/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Saturday
1/10/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Sunday
1/11/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Monday
1/12/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Tuesday
1/13/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Wednesday
1/14/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Thursday
1/15/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Friday
1/16/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Saturday
1/17/2026
8:00 AM | view
tickets |
|
| Mecum Auto Auction | Osceola Heritage Park
Kissimmee, FL | Sunday
1/18/2026
8:00 AM | view
tickets |
|
| Monster Bulls | Silver Spurs Arena
Kissimmee, FL | Saturday
2/14/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Thursday
2/19/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Friday
2/20/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Saturday
2/21/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Sunday
2/22/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Friday
6/5/2026
TBD | view
tickets |
|
| Silver Spurs Rodeo | Silver Spurs Arena
Kissimmee, FL | Saturday
6/6/2026
TBD | view
tickets |
|
