#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.

#31. The Ottawa Senators will reach the 2nd round of the 2017 NHL Playoffs

The Bet: The Ottawa Senators will reach the 2nd round of the 2017 NHL Playoffs

Jimmy: Yes
Tippy: No
Wager: Breakfast
Date: April 7, 2017.

Jimmy is going way out on a limb for this one as Ottawa could still face the Washington Capitals in the 1st round (not likely).
Bolstered by Tip's insistence on having this bet and the recent crushing losses Tip has experienced (see bets 22, 24, 25) Jimmy feels both sympathy and confidence in Tip's ineptness.

GO SENS GO.

Results: Jimmy pads his lead