Biggest Sports Betting Wins — Monday, June 29, 2026
3 notable wins | Total payouts: $117,350 | Total taxes: $29,042
$117,350
Total Payouts
$29,042
Total Taxes
24.7%
Avg Tax Rate
🥇
NHLFutures
$85,000
from $500 wager
futures bet on Knights vs Stars — $500 turned into $85,000
Source: X/TwitterTax Breakdown (Florida)
Net Profit
$84,500
Federal Tax (24%)
-$20,280
State Tax (no tax)
$0
Take-Home
$64,220
OBBBA Note: If this bettor had $84,500 in losses elsewhere, they'd still owe $2,028 in 'phantom income' tax under 2026 OBBBA rules.
🥈
NFL9-Leg Parlay
$30,500
from $100 wager
9-leg parlay on Chiefs vs Bills — $100 turned into $30,500
Source: RedditTax Breakdown (Pennsylvania)
Net Profit
$30,400
Federal Tax (24%)
-$7,296
State Tax
-$933
Take-Home
$22,171
OBBBA Note: If this bettor had $30,400 in losses elsewhere, they'd still owe $730 in 'phantom income' tax under 2026 OBBBA rules.
🥉
MLB4-Leg SGP
$1,850
from $10 wager
4-leg SGP on Dodgers vs Padres — $10 turned into $1,850
Source: RedditTax Breakdown (Illinois)
Net Profit
$1,840
Federal Tax (24%)
-$442
State Tax
-$91
Take-Home
$1,307