Lines move at halftime and you have to just go quickly to beat the steam. When Tomato first saw it, it was -105. He punches in 5k, clicks submit, but there was a line change to -110. Clicks submit again. Realizes he can get down more money, miscalculates, has to do another wager. The total wagers add up to 5499.99 to win 5000.
Same thing with the 2:33 wager. Pressed submit for 5500 on what was a -110, moved to -115, clicks submit, then puts more money down. Wagers add up to 5750 to win 5000.