#38. The Nashville Predators will defeat the Anaheim Ducks in game 1 of the 2017 NHL Playoffs

Tippy: Yes
Chuck: No
Wager: Breakfast
Date: May 11, 2017.

Results: Tippy wins!

Could this be the Tippy TSN turning point?

#37. Brendon Shanahan never played hockey for the Hartford Whalers

Davey: Yes he did!
Tippy: No he didn't!
Wager: Chocolate bar
Date: May 12, 2017.

For God's sake, he was the captain!

"The losing will continue until winning is realized."
(loosely based on a Mike F quote)

#36. The Edmonton Oilers will defeat the Anaheim Ducks in game 7 of the 2017 NHL Playoffs

The Bet:  The Edmonton Oilers will defeat the Anaheim Ducks in game 7 of the 2017 NHL Playoffs

Jimmy: Yes
Chuck: No
Wager: Breakfast
Date: May 10, 2017.

Chuck wins.

#35. The Washington Capitals will defeat the Pittsburgh Penguins in the game 7 of the 2017 NHL Playoffs

The Bet: The Washington Capitals will defeat the Pittsburgh Penguins in the game 7 of the 2017 NHL Playoffs

Tippy: Yes
Chuck: No
Wager: Breakfast
Date: May 10, 2017.

Chuck wins:

Tip, "the master of disaster!"

#34. The Washington Capitals will defeat the Toronto Maple Leafs in the 2017 NHL Playoffs

The Bet: The Washington Capitals will defeat the Toronto Maple Leafs in the 2017 NHL Playoffs.

Given the absurdity of the bet Tippy has given Jimmy a 2 game cushion.
In other words Washington will have to win by at least 3 games (4-1)  for Tip to win.
A 4-2 outcome will mean a push (no one wins).
Anything else and Jimmy gets fatter.

Tippy: Yes
Jimmy: No
Wager: Breakfast
Date: April 13, 2017.

Results: It is a push.

While Washington did win the series 4-2, because of the 2 game cushion it is a tie.

#33. The Calgary Flames will defeat the Anaheim Ducks in the 2017 NHL Playoffs

The Bet: The Calgary Flames will defeat the Anaheim Ducks in the 2017 NHL Playoffs

Tippy: Yes
Chuck: No
Wager: Breakfast
Date: April 13, 2017.

Result:

Tip owes Chuck 1 breakfast

#32. The Edmonton Oilers will defeat the San Jose Sharks in the 2017 NHL Playoffs

The Bet: The Edmonton Oilers will defeat the San Jose Sharks in the 2017 NHL Playoffs

Baggy: Yes
Tippy: No
Wager: Breakfast
Date: April 13, 2017.

Results: Baggy gets in on the Tippy action with a definitive win.